Pest control composition including novel iminopyridine derivative

ABSTRACT

Provided is a pest control composition containing a novel iminopyridine derivative and other pest control agents. 
     Provided is a pest control composition containing an iminopyridine derivative represented by the following Formula (I) and at least one of other pest control agents: 
     
       
         
         
             
             
         
       
         
         
           
             [in the formula (I), Ar represents a 5- to 6-membered heterocycle which may be substituted, A represents a heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms, and has an imino group substituted with an R group at a position adjacent to the nitrogen atom present on the cycle, Y represents hydrogen, halogen and the like, and R represents any one of groups represented by the following Formulae (a) to (e), (y) or (z)].

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of U.S. application Ser. No.15/051,730, filed Feb. 24, 2016, which is a Continuation of U.S.application Ser. No. 14/320,808, filed Jul. 1, 2014, (now U.S. Pat. No.9,301,525); which is a Continuation of PCT/JP2013/056051, filed Feb. 27,2013; the entire disclosures of each of which are hereby incorporatedherein by reference.

BACKGROUND OF THE INVENTION Field of the Invention

The present invention relates to a pest control composition containing anovel iminopyridine derivative and at least one of other pest controlagents.

Related Background Art

Although numerous pest control agents have been discovered so far, thedevelopment of novel drugs which has high safety is still required inview of the problem of reduction in drug sensitivity, the issue oflong-term efficacy, safety to workers or safety in terms ofenvironmental impacts. Further, in agriculture, in order to achieve areduction in labor for the pest control work, it is general to mix aplurality of components of a chemical for pest control and treat seedsor farm products during the growing seedling period with the chemical,and under these circumstances, it is required to use a long-termresidual efficacy type chemical having penetrating and migratingproperty. In addition, it is also possible to solve problems such asscattering of a chemical to the surrounding environment outsideagricultural land or exposure to a person who performs pest control byseed treatment or treatment during the growing seedling period.

European Patent Application Laid-Open No. 432600 (PTL1) discloses aplurality of compounds having the same ring structure as that of acompound represented by Formula (I), but the compounds are used asherbicides and there is no description about pest control.

Japanese Patent Application Laid-Open (JP-A) No. 5-78323 (PTL2)discloses the structural formula ofN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound No. 3 in Table 1 of JP-A No. 5-78323), but fails to disclose apreparation method thereof and the compound is not included in a list ofthe group of compounds that are recognized to have pest control activity(Tables 2 and 3 of JP-A No. 5-78323).

European Patent Application Laid-Open No. 268915 (PTL3) discloses thestructural formula ofN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Example No. 12 in Table 7 of European Patent Application Laid-Open No.268915), but fails to disclose a preparation method thereof and theExample does not include the compound as an example of the compoundshaving pest control activity.

Chemische Berichte (1955), 88, 1103-8 (NPL1) discloses a plurality ofcompounds having a ring structure similar to that of a compoundrepresented by Formula (I) to be described below, but the compounds aredisclosed only as synthetic intermediates.

European Patent Application Laid-Open No. 259738 (PTL4) discloses aplurality of compounds having a ring structure similar to that of acompound represented by Formula (I), but fails to disclose or suggest acompound having a trifluoroacetic acid imino structure.

Furthermore, these documents do not describe pest control activity whenthe novel iminopyridine derivative of the present invention is mixedwith another pest control agent.

SUMMARY OF THE INVENTION

The present invention is contrived to provide a novel pest control agentto solve problems which chemicals in the related art have, such asreduction in drug sensitivity, long-term efficacy, safety during the usethereof and the like in the field of pest control.

In order to solve the problems, the present inventors have intensivelystudied, and as a result, have found that a novel iminopyridinederivative represented by Formula (I) has excellent pest control effectsagainst pests and discovered a composition showing excellent pestcontrol effects by containing these novel iminopyridine derivatives andat least one of other pest control agents, compared to when a singleagent is used, and a use method thereof. The present invention is basedon the finding.

Therefore, an object of the present invention is to provide a pestcontrol composition prepared by containing at least one of a noveliminopyridine derivative represented by the following Formula (I) oracid addition salts thereof and at least one of other pest controlagents, which is used in a low dose and shows excellent pest controleffects against a wide range of pests.

(1) There is provided a pest control composition containing at least oneof a novel iminopyridine derivative represented by the following Formula(I) or acid addition salts thereof as an active ingredient and at leastone of other pest control agents:

[in the formula (I), Ar represents a phenyl group which may besubstituted, a 5- to 6-membered heterocycle which may be substituted, ora 4- to 10-membered heterocycloalkyl group,

A represents a heterocycle having a 5- to 10-membered unsaturated bondincluding one or more nitrogen atoms, and has an imino group substitutedwith an R group at a position adjacent to the nitrogen atom present onthe cycle,

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 toC6 alkyl group which may be substituted with a halogen atom, a C1 to C6alkyloxy group which may be substituted with a halogen atom, a cyanogroup, or a nitro group, and

R represents any one of groups represented by the following Formulae (a)to (e), (y) or (z),

[here, R1 represents a hydrogen atom, a substituted C1 to C6 alkylgroup, a C2 to C6 alkenyl group which may be substituted with a halogenatom, a C2 to C6 alkynyl group which may be substituted with a halogenatom, or a pentafluorophenyl group,

R2 represents a C1 to C6 alkyl group substituted with a halogen atom, anunsubstituted C3 to C6 branched or cyclic alkyl group, a C2 to C6alkenyl group which may be substituted with a halogen atom, a C2 to C6alkynyl group which may be substituted with a halogen atom, asubstituted or unsubstituted (C6 to C10) aryl group, a substituted orunsubstituted 5- to 10-membered heterocycle, or a substituted orunsubstituted benzyl group,

R3 represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C2 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a substituted or unsubstituted (C6 to C10) aryl group, asubstituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, asubstituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group,a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynylgroup, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkenyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkynyl group, asubstituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, ora (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R4 represents a hydrogen atom, a formyl group, a C1 to C6 alkyl groupwhich may be substituted, a C2 to C6 alkenyl group which may besubstituted with a halogen atom, a C2 to C6 alkynyl group which may besubstituted with a halogen atom, a substituted or unsubstituted (C6 toC10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 toC6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 toC6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6)alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenylgroup, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group,a substituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a(C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented byany of the following Formulae (f) to (n)

here, R4a, R4b and R4c represent a C1 to C6 alkyl group which may besubstituted with a halogen atom, a C2 to C6 alkenyl group which may besubstituted with a halogen atom, a C2 to C6 alkynyl group which may besubstituted with a halogen atom, a substituted or unsubstituted (C6 toC10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 toC6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 toC6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6)alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenylgroup, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group,a substituted or unsubstituted 5- to 10-membered heterocycle group, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, ora (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R4d represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C2 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a substituted or unsubstituted (C6 to C10) aryl group, ora substituted or unsubstituted 5- to 10-membered heterocycle, and

R4e and R4f each independently represent a hydrogen atom, a C1 to C6alkyl group which may be substituted with a halogen atom, a C2 to C6alkenyl group which may be substituted with a halogen atom, a C2 to C6alkynyl group which may be substituted with a halogen atom, asubstituted or unsubstituted (C6 to C10) aryl group, or a substituted orunsubstituted 5- to 10-membered heterocycle,

R5 represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C1 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a substituted or unsubstituted (C6 to C10) aryl group, asubstituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, asubstituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group,a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynylgroup, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkenyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkynyl group, asubstituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, ora (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R6 represents a hydrogen atom, a formyl group, a 0,0′-C1 to C4 alkylphosphoryl group, a C1 to C18 alkyl group which may be substituted, a C2to C6 alkenyl group which may be substituted with a halogen atom, a C2to C6 alkynyl group which may be substituted with a halogen atom, asubstituted or unsubstituted (C6 to C10) aryl group, a substituted orunsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted orunsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substitutedor unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, asubstituted or unsubstituted phenoxy (C1 to C6) alkyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkenyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkynyl group, asubstituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a(C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented byany of the following Formulae (o) to (x)

here, R6a, R6b and R6c represent a C1 to C6 alkyl group which may besubstituted with a halogen atom, a C2 to C6 alkenyl group which may besubstituted with a halogen atom, a C2 to C6 alkynyl group which may besubstituted with a halogen atom, a substituted or unsubstituted (C6 toC10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 toC6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 toC6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6)alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenylgroup, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group,a substituted or unsubstituted 5- to 10-membered heterocycle group, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, anda (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R6d represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C2 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a substituted or unsubstituted (C6 to C10) aryl group, ora substituted or unsubstituted 5- to 10-membered heterocycle,

R6e and R6f each independently represent a hydrogen atom, a C1 to C6alkyl group which may be substituted with a halogen atom, a C2 to C6alkenyl group which may be substituted with a halogen atom, a C2 to C6alkynyl group which may be substituted with a halogen atom, a (C1 to C4)alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C1 to C5) alkylgroup, a substituted or unsubstituted (C6 to C10) aryl group, asubstituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, ora substituted or unsubstituted 5- to 10-membered heterocycle,

R6g and R6h each independently represent a hydrogen atom, a C1 to C6alkyl group which may be substituted with a halogen atom, a C2 to C6alkenyl group which may be substituted with a halogen atom, a C2 to C6alkynyl group which may be substituted with a halogen atom, asubstituted or unsubstituted (C6 to C10) aryl group, or a substituted orunsubstituted 5- to 10-membered heterocycle, and

R6i, R6j and R6k each independently represent a hydrogen atom, a C1 toC6 alkyl group which may be substituted with a halogen atom, a C2 to C6alkenyl group which may be substituted with a halogen atom, a C2 to C6alkynyl group which may be substituted with a halogen atom, or asubstituted or unsubstituted (C6 to C10) aryl group), and

R7 represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C1 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a substituted or unsubstituted (C6 to C10) aryl group, asubstituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, asubstituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group,a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynylgroup, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkenyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkynyl group, asubstituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, ora (C1 to C4) alkylthio (C2 to C5) alkynyl group,

Y1 and Y2 represent an oxygen atom or a sulfur atom, and may be the sameor different, and

Ry represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C2 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a substituted or unsubstituted (C6 to C10) aryl group, asubstituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, asubstituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group,a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynylgroup, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkenyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkynyl group, asubstituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, or a substituted or unsubstituted5- to 10-membered heterocycle (C2 to C6) alkynyl group,

Rz represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C2 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a substituted or unsubstituted (C6 to C10) aryl group, asubstituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, asubstituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group,a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynylgroup, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkenyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkynyl group, asubstituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, ora (C1 to C4) alkylthio (C2 to C5) alkynyl group, and n represents 1 or2],

(2) There is provided the pest control composition according to (1),containing at least one of an amine derivative represented by thefollowing Formula (Ia) or acid addition salts thereof as an activeingredient and at least one of other pest control agents:

[here, Ar represents a pyridyl group which may be substituted with ahalogen atom, a hydroxyl group, a C1 to C6 alkyl group which may besubstituted with a halogen atom, a C1 to C6 alkyloxy group which may besubstituted with a halogen atom, a cyano group, or a nitro group, or apyrimidyl group which may be substituted with a halogen atom, a C1 to C4alkyl group which may be substituted with a halogen atom, an alkyloxygroup which may be substituted with a halogen atom, a hydroxyl group, acyano group, or a nitro group,

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 toC6 alkyl group which may be substituted with a halogen atom, a C1 to C6alkyloxy group which may be substituted with a halogen atom, a cyanogroup, or a nitro group, and

R₁ represents a C1 to C6 alkyl group which is substituted with a halogenatom].

(3) There is provided the pest control composition according to (1),wherein Ar is a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridylgroup, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, or a2-chloro-5-pyrimidyl group.

(4) There is provided the pest control composition according to (1) or(3), wherein in Formula (I), A is the following Formula (A-1):

and Y is a hydrogen atom, a halogen atom, or a cyano group.

(5) There is provided the pest control composition according to (1), (3)to (4), wherein R in Formula (I) is a group with Formula (c).

(6) There is provided the pest control composition according to (1), (3)to (4), wherein R in Formula (I) is a group with Formula (a).

(7) There is provided the pest control composition according to (1), (3)to (4), wherein R in Formula (I) is a group with Formula (d)

and R4 is a C1 to C18 alkyl group which may be substituted, a C2 to C6alkenyl group which may be substituted with a halogen atom, a C2 to C6alkynyl group which may be substituted with a halogen atom, asubstituted or unsubstituted (C6 to C10) aryl group, a substituted orunsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted orunsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substitutedor unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, asubstituted or unsubstituted phenoxy (C1 to C6) alkyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkenyl group, asubstituted or unsubstituted phenoxy (C2 to C6) alkynyl group, asubstituted or unsubstituted 5- to 10-membered heterocycle, asubstituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6)alkyl group, a substituted or unsubstituted 5- to 10-memberedheterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5-to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy(C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a(C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, ora (C1 to C4) alkylthio (C2 to C5) alkynyl group, and

R5 is a C1 to C6 alkyl group which may be substituted with a halogenatom, a C2 to C6 alkenyl group which may be substituted with a halogenatom, a C2 to C6 alkynyl group which may be substituted with a halogenatom, and R5 is a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C2 to C6 alkenyl group which may be substituted with ahalogen atom, or a C2 to C6 alkynyl group which may be substituted witha halogen atom.

(8) There is provided the pest control composition according to (1),wherein the iminopyridine derivative isN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide,N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide,orN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide.

(9) There is provided a method for protecting useful plants or animalsfrom pests, including: treating pests, useful plants, seeds of usefulplants, soil, cultivation carriers or animals as a target with aneffective amount of the pest control composition.

(10) There is provided a combination (combined product) including theiminopyridine derivative represented by Formula (I) and at least one ofother pest control agents.

(11) There is provided a use of the pest control composition forprotecting useful plants or animals from pests.

It is possible to effectively perform pest control against cabbagemoths, Spodoptera litura, aphids, planthoppers, leafhoppers, thrips andother numerous pests by using novel iminopyridine derivative of thepresent invention.

BRIEF DESCRIPTION OF THE DRAWINGS

A novel iminopyridine derivative represented by Formula (I) may beprepared by the following method.

(I-1) may be obtained by reacting a compound represented by thefollowing Formula (II-1) with a compound represented by ArCH2X [thedefinition of Ar, A, Y and R1 has the same meaning as the definitiondescribed above, and X represents a halogen atom or OTs, OMs and thelike] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide, and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when a solvent is used, it is possibleto use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0° C. to 200° C., and it ispreferred that reagents are added at 20° C. to 40° C. and the reactionis performed at 60° C. to 80° C.

The compound represented by Formula (II-1) may be obtained by reacting acompound represented by R1-C(═O)X, R1-C(═O)OC(═O)R1, R1C(═O)OR′ [Xrepresents a halogen atom or OTs, OMs and the like, R′ represents a C1to C6 alkyl group, and the definition of R1, A and Y has the samemeaning as the definition described above] and the like with a compoundrepresented by the following Formula (III) in the presence or absence ofa base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water, either alone or in combination of two ormore thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers,dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C. The compoundrepresented by Formula (II-1) may be obtained by reacting the compoundrepresented by Formula (III) with a carboxylic acid represented byR1-COOH [the definition of R1 has the same meaning as the definitiondescribed above]using a dehydration condensation agent in the presenceor absence of a base, or may be obtained by performing the reactionusing phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionylchloride, phosphorus oxychloride and oxalyl dichloride in the absence ofa base.

It is possible to use a carbodiimide-based compound such asdicyclohexylcarbodiimide and1-ethyl-3-(3-[dimethylaminopropyl])carbodiimide hydrochloride as thedehydration condensation agent.

When the reaction is performed in the presence of a base, it is possibleto use, for example, a carbonate such as potassium carbonate or sodiumcarbonate, tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine, as the base.

The reaction is preferably performed by using a solvent, and it ispossible to use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C. The compoundrepresented by Formula (I-1) may be obtained by reacting a compoundrepresented by R1-C(═O)X, R1-C(═O)OC(═O)R1, R1C(═O)OR′ [X represents ahalogen atom or OTs, OMs and the like, R′ represents a C1 to C6 alkylgroup, and the definition of Ar, A, Y and R1 has the same meaning as thedefinition described above] and the like with a compound represented bythe following Formula (IV) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water, either alone or in combination of two ormore thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers,dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C. The compoundrepresented by Formula (I-1) may be obtained by reacting theabove-described compound represented by Formula (IV) with a carboxylicacid represented by R1-COOH [the definition of R1 has the same meaningas the definition described above] using a dehydration condensationagent in the presence or absence of a base, or may be obtained byperforming the reaction using phosphorus pentaoxide, sulfuric acid,polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyldichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such asdicyclohexylcarbodiimide and1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride as thedehydration condensation agent.

When the reaction is performed in the presence of a base, it is possibleto use, for example, a carbonate such as potassium carbonate or sodiumcarbonate, tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine, as the base.

The reaction is preferably performed by using a solvent, and it ispossible to use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C. The compoundrepresented by Formula (IV) may be obtained by reacting theabove-described compound represented by Formula (III) with a compoundrepresented by ArCH2X [the definition of Ar and X has the same meaningas the definition described above] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water, either alone or in combination of two ormore thereof, but N,N-dimethylformamide, acetonitrile, ethers,dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C.

When Formula (I-1) is synthesized via Formula (II-1) from the compoundrepresented by Formula (III), or when Formula (I-1) is synthesized viaFormula (IV) from the compound represented by Formula (III), thereaction may be continuously performed without taking out Formula (II-1)or Formula (IV), or the reactions from Formula (III) to Formula (I-1)may be simultaneously performed in the same vessel.

The compound represented by Formula (I-2) may be obtained by reacting acompound represented by the following Formula (I-2a) with a compoundrepresented by ArCH2X [the definition of Ar, A, Y and R2 has the samemeaning as the definition described above, and X represents a halogenatom or OTs, OMs and the like] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when a solvent is used, it is possibleto use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0° C. to 200° C., and it ispreferred that reagents are added at 20° C. to 40° C. and the reactionis performed at 60° C. to 80° C.

The compound represented by Formula (I-2a) may be obtained by reactingthe above-described compound represented by Formula (III) with acompound represented by R2OC(═O)X (the definition of R2 and X has thesame meaning as the definition described above] or represented by thefollowing Formula (I-2b) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when a solvent is used, it is possibleto use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether, and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but acetonitrile, dichloromethane or the like is preferably used.

The reaction may be performed usually at 0° C. to 200° C., and isperformed preferably at 20° C. to 80° C.

The compound represented by Formula (I-2) may be obtained by reactingthe above-described compound represented by Formula (IV) with a compoundrepresented by R2OC(═O)X (the definition of R2 and X has the samemeaning as the definition described above] or represented by theabove-described Formula (I-2b) in the presence or absence of a base.When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when a solvent is used, it is possibleto use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but acetonitrile, dichloromethane or the like is preferably used.

The reaction may be performed usually at 0° C. to 200° C., and isperformed preferably at 20° C. to 80° C.

The compound represented by Formula (I-3) may be synthesized by acting asulfurizing reagent on a compound (the definition of Ar, A, Y and R3 hasthe same meaning as the definition described above) represented by thefollowing Formula (II-3a), which may be synthesized in the same manneras described in Formula (I-1), in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base, but potassium carbonate, sodiumcarbonate or the like is preferably used.

As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent,hydrogen sulfide and the like may be used.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when a solvent is used, it is possibleto use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol and propanol, ketones suchas acetone and methyl ethyl ketone, aliphatic hydrocarbons such ashexane, heptane and octane, and halogen hydrocarbons such asdichloromethane, chloroform, chlorobenzene and dichlorobenzene, eitheralone or in combination of two or more thereof, but toluene,tetrahydrofuran or the like is preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C. The compoundrepresented by Formula (I-3) may be obtained by reacting a compoundrepresented by the following Formula (II-3b) with a compound representedby ArCH2X [the definition of Ar, A, Y and R3 has the same meaning as thedefinition described above, and X represents a halogen atom or OTs, OMsand the like] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when a solvent is used, it is possibleto use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0° C. to 200° C., and it ispreferred that reagents are added at 20° C. to 40° C. and the reactionis performed at 60° C. to 80° C.

The compound represented by Formula (II-3b) may be synthesized by actinga sulfurizing reagent on a compound (the definition of A, Y and R3 hasthe same meaning as the definition described above) represented byFormula (II-3c), which may be synthesized in the same manner asdescribed in Formula (II-1), in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base, but potassium carbonate, sodiumcarbonate or the like is preferably used.

As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent,hydrogen sulfide and the like may be used. The reaction may be performedwithout a solvent or using a solvent which does not affect the reaction,and when a solvent is used, it is possible to use solvents such as, forexample, amides such as N,N-dimethylformamide and N,N-dimethylacetamide,nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide,ethers such as diethyl ether and tetrahydrofuran, esters such as ethylacetate and butyl acetate, aromatic hydrocarbons such as benzene, xyleneand toluene, alcohols such as methanol, ethanol and propanol, ketonessuch as acetone and methyl ethyl ketone, aliphatic hydrocarbons such ashexane, heptane and octane, and halogen hydrocarbons such asdichloromethane, chloroform, chlorobenzene and dichlorobenzene, eitheralone or in combination of two or more thereof, but toluene,tetrahydrofuran and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (I-4) may be obtained by reacting acompound represented by the following Formula (II-4a), which may besynthesized in the same manner as described in Formula (I-3) with acompound represented by R4-NH2 (the definition of Ar, A, Y, R4 and R5has the same meaning as the definition described above).

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when a solvent is used, it is possibleto use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol and propanol, ketones suchas acetone and methyl ethyl ketone, aliphatic hydrocarbons such ashexane, heptane and octane, and halogen hydrocarbons such asdichloromethane, chloroform, chlorobenzene and dichlorobenzene, eitheralone or in combination of two or more thereof, but alcohols such asmethanol and ethanol are preferably used.

The reaction, if performed in the presence of silver carbonate, coppercarbonate and the like, progresses quickly, but may proceed without thecompound.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (I-4) may be obtained by reacting acompound represented by the following Formula (I-4b) or a salt thereofwith R4-X, R4-O—R4 and R4-OR′ (the definition of R4, R′, Ar, A, Y and R5has the same meaning as the definition described above, and X representsa halogen atom) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water either alone or in combination of two ormore thereof, but toluene, dimethylformamide, acetonitrile, ethers,dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C. The compoundrepresented by Formula (I-4b) may be obtained by reacting a compoundrepresented by Formula (II-4a) with ammonia or an alcohol solutionthereof, ammonium chloride and the like.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water, either alone or in combination of two ormore thereof, but alcohols such as methanol and ethanol are preferablyused.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C.

The compound represented by Formula (I-5) may be obtained by reacting acompound represented by the following Formula (II-5b) with R6-X (thedefinition of AR, A, Y, R6 and R7 has the same meaning as the definitiondescribed above, and X represents a halogen atom), R6-O—R6 or R6-OR′(the definition of R′ has the same meaning as the definition describedabove) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water, either alone or in combination of two ormore thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers,dichloromethane and chloroform are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C.

When R6 represents —C(═O)R6a (R6a has the same meaning as describedabove), the compound represented by Formula (I-5) may be obtained byreacting the compound represented by Formula (II-5b) with a carboxylicacid represented by R6a-C(═O)OH (the definition of R6a has the samemeaning as the definition described above) using a dehydrationcondensation agent in the presence or absence of a base, or may beobtained by performing the reaction using phosphorus pentaoxide,sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorusoxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such asdicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride and the like as the dehydration condensation agent.

When the reaction is performed in the presence of a base, it is possibleto use, for example, a carbonate such as potassium carbonate or sodiumcarbonate, tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction is preferably performed by using a solvent, and it ispossible to use, for example, amides such as N,N-dimethylformamide andN,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such asdimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran,esters such as ethyl acetate and butyl acetate, aromatic hydrocarbonssuch as benzene, xylene and toluene, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,and halogen hydrocarbons such as dichloromethane, chloroform,chlorobenzene and dichlorobenzene, either alone or in combination of twoor more thereof, but dichloromethane, chloroform and the like arepreferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 50° C.

When R6 represents CONR6eR6f (the definition of R6e and R6f has the samemeaning as the definition described above, and R6e or R6f represents ahydrogen atom) or CSNR6gR6h (the definition of R6g and R6h has the samemeaning as the definition described above, and R6g or R6h represents ahydrogen atom), the compound of Formula (I-5) may be obtained byreacting the Formula (II-5b) with a compound represented by R″N═C═O (R″represents a C1 to C6 alkyl group which may be substituted with ahalogen atom, a C2 to C6 alkenyl group which may be substituted with ahalogen atom, a C2 to C6 alkynyl group which may be substituted with ahalogen atom, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4)alkylthio (C1 to C5) alkyl group, a substituted or unsubstituted (C6 toC10) aryl group, and a substituted or unsubstituted 5- to 10-memberedheterocycle) in the presence or absence of a base. When the reaction isperformed in the presence of a base, it is possible to use, for example,an alkali metal hydride such as sodium hydride, a carbonate such aspotassium carbonate or sodium carbonate, an alkali metal hydroxide suchas potassium hydroxide and sodium hydroxide, tertiary amines such astriethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base. The reaction is preferablyperformed by using a solvent, and it is possible to use, for example,amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitrilessuch as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers suchas diethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but nitriles such as acetonitrile are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C.

When R6 represents CONR6eR6f (the definition of R6e and R6f has the samemeaning as the definition described above), the compound of Formula(I-5) may be obtained by reacting the above-described compoundrepresented by Formula (II-5b) with a compound represented by thefollowing Formula (II-5c) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction is preferably performed by using a solvent, and it ispossible to use, for example, amides such as N,N-dimethylformamide andN,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such asdimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran,esters such as ethyl acetate and butyl acetate, aromatic hydrocarbonssuch as benzene, xylene and toluene, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,and halogen hydrocarbons such as dichloromethane, chloroform,chlorobenzene and dichlorobenzene, either alone or in combination of twoor more thereof, but nitriles such as acetonitrile are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (II-5b) may be obtained by reactingthe compound (the definition of Ar, A, Y and R7 has the same meaning asthe definition described above) represented by Formula (II-5a), whichmay be synthesized in the same manner as described in Formula (I-3) withhydroxylamine or a salt thereof in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water, either alone or in combination of two ormore thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers,dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (I-5) may also be obtained byreacting the compound represented by Formula (II-5a) with a compoundrepresented by R6-ONH2 or a salt thereof in the presence or absence of abase.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride, acarbonate such as potassium carbonate or sodium carbonate, an alkalimetal hydroxide such as potassium hydroxide and sodium hydroxide,tertiary amines such as triethylamine and1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction. When a solvent is used, it is possible touse solvents such as, for example, amides such as N,N-dimethylformamideand N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxidessuch as dimethyl sulfoxide, ethers such as diethyl ether andtetrahydrofuran, esters such as ethyl acetate and butyl acetate,aromatic hydrocarbons such as benzene, xylene and toluene, alcohols suchas methanol, ethanol and propanol, ketones such as acetone and methylethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane,halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzeneand dichlorobenzene, and water, either alone or in combination of two ormore thereof, but alcohols such as methanol and ethanol are preferablyused.

The reaction may be performed usually at −80° C. to 100° C., and isperformed preferably in a range from 20° C. to 80° C.

The reaction, if performed in the presence of silver carbonate, coppercarbonate and the like, progresses quickly, but may proceed without thecompound.

The compound represented by Formula (I-6) [the definition of Ar, A, Y,Y1, Y2, and Ry has the same meaning as the definition described above]may be obtained by reacting according to Phosphorus, sulfur, and siliconand the related elements (2006) 181, 2337-2344.

The compound represented by Formula (I-7) [the definition of Ar, A, Y,Ry and n has the same meaning as the definition described above] may beobtained by reacting a compound represented by the following Formula(II-7a) with a compound represented by ArCH2X [the definition of Ar hasthe same meaning as the definition described above, and X represents ahalogen atom or OTs, OMs and the like] in the presence or absence of abase.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride andthe like, a carbonate such as potassium carbonate or sodium carbonateand the like, an alkali metal hydroxide such as potassium hydroxide,sodium hydroxide and the like, tertiary amines such as triethylamine,1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted orsubstituent-containing pyridines, such as pyridine,4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when the solvent is used, it ispossible to use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0° C. to 200° C., and itis preferred that reagents are added at from 20° C. to 40° C. and thereaction is performed at from 60° C. to 80° C.

The compound represented by Formula (II-7a) may be obtained by reactinga compound represented by (II-7b) [X represents a halogen atom, and thedefinition of Rz and n has the same meaning as the definition describedabove] with a compound represented by in the following Formula (III) inthe presence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride andthe like, a carbonate such as potassium carbonate or sodium carbonateand the like, an alkali metal hydroxide such as potassium hydroxide,sodium hydroxide and the like, tertiary amines such as triethylamine,1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted orsubstituent-containing pyridines, such as pyridine,4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when the solvent is used, it ispossible to use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0° C. to 200° C., and itis preferred that reagents are added at from 20° C. to 40° C. and thereaction is performed at from 60° C. to 80° C.

The compound represented by Formula (I-7) may be obtained by reacting acompound represented by (II-7b) [X represents a halogen atom, and thedefinition of Rz has the same meaning as the definition described above]with a compound represented by in the following Formula (IV) in thepresence or absence of a base.

When the reaction is performed in the presence of a base, it is possibleto use, for example, an alkali metal hydride such as sodium hydride andthe like, a carbonate such as potassium carbonate or sodium carbonateand the like, an alkali metal hydroxide such as potassium hydroxide,sodium hydroxide and the like, tertiary amines such as triethylamine,1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted orsubstituent-containing pyridines, such as pyridine,4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent whichdoes not affect the reaction, and when the solvent is used, it ispossible to use solvents such as, for example, amides such asN,N-dimethylformamide and N,N-dimethylacetamide, nitriles such asacetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such asdiethyl ether and tetrahydrofuran, esters such as ethyl acetate andbutyl acetate, aromatic hydrocarbons such as benzene, xylene andtoluene, alcohols such as methanol, ethanol, propanol and isopropylalcohol, ketones such as acetone and methyl ethyl ketone, aliphatichydrocarbons such as hexane, heptane and octane, and halogenhydrocarbons such as dichloromethane, chloroform, chlorobenzene anddichlorobenzene, either alone or in combination of two or more thereof,but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0° C. to 200° C., and itis preferred that the reaction is performed at from 0° C. to 80° C.

Examples of a substituent that may be substituted of “a phenyl groupwhich may be substituted” and “a 5- to 6-membered heterocycle which maybe substituted”, which are represented by Ar, include a halogen atom, aC1 to C4 alkyl group which may be substituted with a halogen atom, a C1to C4 alkyloxy group which may be substituted with a halogen atom, ahydroxyl group, a cyano group, a nitro group and the like, preferably ahalogen atom, a trifluoromethyl group and a cyano group, andparticularly preferably a halogen atom.

Specific examples of the “a phenyl group which may be substituted”represented by Ar of a nitrogen-containing heterocyclic derivativecompound having a 2-imino group represented by Formula (I) include aphenyl group and a 3-cyano phenyl group.

“A 5- to 6-membered heterocycle which may be substituted”, representedby Ar of a nitrogen-containing heterocyclic derivative compound having a2-imino group represented by Formula (I) represents an aromatic 5- to6-membered heterocycle including one or two of a heteroatom such as anoxygen atom, a sulfur atom or a nitrogen atom, specific examples thereofinclude a pyridine ring, a pyrazine ring, a pyrimidine ring, apyridazine ring, a thiazole ring, an oxazole ring and the like, andpreferable aspects thereof include a 6-chloro-3-pyridyl group, a6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a6-fluoro-3-pyridyl group, a 6-trifluoromethyl-3-pyridyl group, a6-chloro-3-pyridazinyl group, a 5-chloro-2-pyrazinyl group, a2-chloro-5-pyrimidinyl group, a 2-chloro-5-thiazolyl group, a2-chloro-4-pyridyl group, and more preferably a 6-chloro-3-pyridylgroup, a 6-fluoro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group,a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidinyl group.

Specific examples of “a 4- to 10-membered heterocycloalkyl group”represented by Ar of a nitrogen-containing hetero ring derivative havinga 2-imino group represented by Formula (I) include a 2-tetrahydrofuranylgroup, a 3-tetrahydrofuranyl group and the like and preferably a3-tetrahydrofuranyl group. “A heterocycle having a 5- to 10-memberedunsaturated bond including one or more nitrogen atoms”, which A of anitrogen-containing heterocyclic derivative having a 2-imino grouprepresented by Formula (I) represents, means that

in Formula (I) represents any one ring represented by each of thefollowing Formulae A-1 to A-40. In each formula, the end of a doublebond is the substitution position of a nitrogen atom.

The ring is preferably the ring of Formulae A-1, A-13, A-14, A-15, A-16,A-23, A-25, A-38 and A-39 and more preferably the ring of Formula A-1.

“A C1 to C6 alkyl group which may be substituted with a halogen atom”,which Y represents, is an alkyl group having 1 to 6 carbon atoms, whichis chained, branched, cyclic or combination thereof, and the upper limitof the number of halogen atoms which may be substituted is the number ofhydrogen atoms which the alkyl group has. When a branched or cyclicalkyl group is included, it is obvious that the number of carbons is 3or more.

Specific examples of “a C1 to C6 alkyloxy group which may be substitutedwith a halogen atom” which Y represents include a methoxy group, anethoxy group, a trifluoromethyloxy group and a difluoromethyloxy group.

A preferred aspect of Y is preferably a hydrogen atom or a halogen atomand more preferably a hydrogen atom.

A preferred aspect of R is a group represented by the Formula (a), (c)and (d) described above.

in Formula (I), “a substituted C1 to C6 alkyl group” which R1 representsis an alkyl group having 1 to 6 carbon atoms, which is chained,branched, cyclic or combination thereof, and the upper limit of thenumber of substituted substituents is the number of hydrogen atoms whichthe alkyl group has. Examples of the substituted substituent include ahalogen atom, a hydroxyl group, a cyano group, a nitro group, a phenylgroup (this phenyl group may be substituted with a C1 to C4 alkyl groupwhich may be substituted with a halogen, a C1 to C4 alkyloxy group whichmay be substituted with a halogen, a hydroxyl group, or a halogen atom),a phenoxy group (this phenyl group may be substituted with a C1 to C4alkyl group which may be substituted with a halogen, a C1 to C4 alkyloxygroup which may be substituted with a halogen, a hydroxyl group, or ahalogen atom), a benzyloxy group (the phenyl group in this benzyloxygroup may be substituted with a C1 to C4 alkyl group which may besubstituted with a halogen, a C1 to C4 alkyloxy group which may besubstituted with a halogen, a hydroxyl group, or a halogen atom), andthe like. Specific examples thereof include a 1,1,1-trifluoroethylgroup, a trifluoromethyl group, a trichloromethyl group, adifluorochloromethyl group, a difluoromethyl group, a dichloromethylgroup, a dibromomethyl group, a chloromethyl group, a difluoroethylgroup, a dichloroethyl group, a 2,2,2-trifluoroethyl group, apentafluoroethyl group, a difluorocyclopropyl group, a 2-cyanoethylgroup, a 2-nitroethyl group and the like. A 1,1,1-trifluoroethyl group,a trifluoromethyl group, a difluorochloromethyl group, a difluoromethylgroup and a pentafluoroethyl group are preferred, a trifluoromethylgroup, a difluorochloromethyl group, a difluoromethyl group and apentafluoroethyl group are more preferred, and a trifluoromethyl groupare particularly preferred.

In Formula (I), “a C1 to C6 alkyl group which may be substituted with ahalogen atom” which R3, R5, R7, Ry, and Rz represent is an alkyl grouphaving 1 to 6 carbon atoms, which is chained, branched, cyclic orcombination thereof, and the upper limit of the number of substitutedhalogen atoms is the number of hydrogen atoms which the alkyl group has.When a branched or cyclic alkyl group is included, it is obvious thatthe number of carbons is 3 or more. Specific examples thereof include amethyl group, an ethyl group, an n-propyl group, an isopropyl group, ann-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentylgroup, a cyclohexyl group, a trifluoromethyl group, a trichloromethylgroup, a difluorochloromethyl group, a difluoromethyl group, adichloromethyl group, a dibromomethyl group, a chloromethyl group, adifluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethylgroup, a pentafluoroethyl group, a difluorocyclopropyl group, atrifluoroisopropyl group, and a hexafluoroisopropyl group, and the like.

R3 is each preferably an ethyl group, an isopropyl group, a cyclopropylgroup, a trifluoromethyl group, a difluorochloromethyl group, adifluoromethyl group and a pentafluoroethyl group, more preferably atrifluoromethyl group, a difluorochloromethyl group, a difluoromethylgroup and a pentafluoroethyl group, and particularly preferably atrifluoromethyl group. R5 is preferably a trifluoromethyl group, atrichloromethyl group, a dichloromethyl group, a difluoromethyl group, adifluorochloromethyl group, a chloromethyl group and a pentafluoroethylgroup, more preferably a trifluoromethyl group, a difluoromethyl group,a difluorochloromethyl group and a pentafluoroethyl group, andparticularly preferably a trifluoromethyl group. R7 is preferably atrifluoromethyl group, a trichloromethyl group, a dichloromethyl group,a difluoromethyl group, a difluorochloromethyl group, a chloromethylgroup and a pentafluoroethyl group, more preferably a trifluoromethylgroup, a difluoromethyl group, a difluorochloromethyl group and apentafluoroethyl group, and particularly preferably a trifluoromethylgroup.

Ry is preferably a methyl group, ethyl group, propyl group or isopropylgroup. Rz is preferably a methyl group or trifluoromethyl group.

“A C1 to C6 alkyl group which may be substituted with a halogen atom”,which R2 represents, is an alkyl group having 1 to 6 carbon atoms, whichis chained, branched, cyclic or combination thereof, and the upper limitof the number of substituted halogen atoms is the number of hydrogenatoms which the alkyl group has. When a branched or cyclic alkyl groupis included, it is obvious that the number of carbons is 3 or more.Specific examples thereof include a trifluoromethyl group, atrichloromethyl group, a difluorochloromethyl group, a difluoromethylgroup, a dichloromethyl group, a dibromomethyl group, a chloromethylgroup, a difluoroethyl group, a dichloroethyl group, a2,2,2-trifluoroethyl group, a pentafluoroethyl group, adifluorocyclopropyl group, a 1-(trifluoromethyl)ethyl group, a1-trifluoromethyl-2,2,2-trifluoroethyl group, a pentafluoroethyl group,and a difluorocyclopropyl group, and the like, and preferred examplesthereof include a 2,2,2-trifluoroethyl group, a 1-(trifluoromethyl)ethylgroup and a 1-trifluoromethyl-2,2,2-trifluoroethyl group.

“A C1 to C6 alkyl group which may be substituted” which R4 and R6represent is an alkyl group having 1 to 18 carbon atoms, which ischained, branched, cyclic or combination thereof, and the upper limit ofthe number of substituents which may be substituted is the number ofhydrogen atoms which the alkyl group has. When a branched or cyclicalkyl group is included, it is obvious that the number of carbons is 3or more. Examples of the substituent which may be substituted include ahalogen atom, a hydroxyl group, a cyano group, a nitro group and thelike. Specific examples thereof include a methyl group, an ethyl group,an n-propyl group, an isopropyl group, an n-butyl group, an s-butylgroup, a t-butyl group, a 3-methyl-2-butyl group, a 3-pentyl group, a4-heptyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentylgroup, a cyclohexyl group, an n-octyl group, an n-tridecyl group, ann-hexadecyl group, an n-octadecyl group, a trifluoromethyl group, atrichloromethyl group, a difluorochloromethyl group, a difluoromethylgroup, a dichloromethyl group, a dibromomethyl group, a chloromethylgroup, a difluoroethyl group, a dichloroethyl group, a2,2,2-trifluoroethyl group, a pentafluoroethyl group, adifluorocyclopropyl group, a 2-hydroxyethyl group, a 2-hydroxy-n-propylgroup, a 3-hydroxy-n-propyl group, a 2,3-dihydroxy-n-propyl group, acyanomethyl group, a 2-cyanoethyl group, a 2-nitroethyl group and thelike.

R4 is each preferably a methyl group, an ethyl group, a2,2,2-trifluoroethyl group, a 2,2-difluoroethyl group, an n-propylgroup, an isopropyl group, a cyclopropyl group, a t-butyl group, acyclopentyl group, a cyclohexyl group and a 2-hydroxyethyl group, andmore preferably a methyl group, an ethyl group and a cyclopropyl group.R6 is preferably a methyl group, an ethyl group, an isopropyl group acyclopropyl group, a t-butyl group and a cyanomethyl group, and morepreferably a methyl group, an ethyl group, a cyclopropyl group and at-butyl group.

“A C1 to C6 alkyl group which may be substituted with a halogen atom”,which R4a, R4b, R4c, R4d, R4e, R4f, R6a, R6b, R6c, R6d, R6e, R6f, R6g,R6h, R6i, R6j and R6k represent, is an alkyl group having 1 to 6 carbonatoms, which is chained, branched, cyclic or combination thereof, andthe upper limit of the number of substituted halogen atoms is the numberof hydrogen atoms which the alkyl group has. When a branched or cyclicalkyl group is included, it is obvious that the number of carbons is 3or more. Specific examples thereof include a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, at-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexylgroup, a trifluoromethyl group, a trichloromethyl group, adifluorochloromethyl group, a difluoromethyl group, a dichloromethylgroup, a dibromomethyl group, a chloromethyl group, a difluoroethylgroup, a 2-chloroethyl group, a dichloroethyl group, a2,2,2-trifluoroethyl group, a pentafluoroethyl group, adifluorocyclopropyl group and the like. R6a is preferably a methylgroup, an ethyl group, an isopropyl group and a cyclopropyl group. R6bis preferably a methyl group.

“A C2 to C6 alkenyl group which may be substituted with a halogen atom”,which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b,R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j, R6k, R7, Ry and Rz represent, isan alkenyl group having 2 to 6 carbon atoms, which is chained, branched,cyclic or combination thereof, and the upper limit of the number ofsubstituted halogen atoms is the number of hydrogen atoms which thealkenyl group has. When a branched or cyclic alkenyl group is included,it is obvious that the number of carbons is 3 or more. Specific examplesthereof include an ethenyl group, a 1-propenyl group, a 2-propenylgroup, a 2-fluoro-1-propenyl group, a 2-methyl-1-propenyl group and thelike, and preferred examples thereof include an ethenyl group.

“A C2 to C6 alkynyl group which may be substituted with a halogen atom”,which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b,R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j, R6k, R7, Ry and Rz represent, isan alkynyl group having 2 to 6 carbon atoms, which is chained, branched,cyclic or combination thereof, and the upper limit of the number ofsubstituted halogen atoms is the number of hydrogen atoms which thealkynyl group has. When a branched or cyclic alkynyl group is included,it is obvious that the number of carbons is 3 or more. Specific examplesthereof include a 1-propynyl group, a 2-propynyl group, a 1-butynylgroup, a 2-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a3-pentynyl group and the like, and preferred examples thereof include a1-propynyl group, a 2-propynyl group and a 2-butynyl group.

The (C6 to C10) aryl of “a substituted or unsubstituted (C6 to C10) arylgroup, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkylgroup, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6)alkenyl group and a substituted or unsubstituted (C6 to C10) aryl (C2 toC6) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c,R7, Ry and Rz represent, specifically represents a phenyl group and anaphthyl group, and the (C1 to C6) alkyl group, the (C2 to C6) alkenylgroup and the (C2 to C6) alkynyl group may have a straight chain, branchor ring. Examples of the substituent which may be substituted with anaryl group include a halogen atom, a C1 to C4 alkyl group which may besubstituted with halogen, a C1 to C4 alkyloxy group which may besubstituted with halogen, a C3 to C6 cyclic alkyl group, amethylsulfonyl group, a methoxy group, a nitro group, a cyano group andthe like. Specific examples thereof include a phenyl group, a benzylgroup, a 2-phenylethyl group, a 2-phenylethenyl group, a 2-phenylethynylgroup, a 4-methylphenyl group, a 2-cyanophenyl group, a 3-chlorophenylgroup, a 4-methoxyphenyl group, a 3-cyanophenyl group,1,1-diphenylmethyl group, a naphthylethyl group, a naphthylpropyl groupand the like, and preferred examples thereof include a benzyl group anda 2-phenylethyl group, a naphthylethyl group, a naphthylpropyl group.

The (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6)alkenyl group of “a substituted or unsubstituted phenoxy (C1 to C6)alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenylgroup and a substituted or unsubstituted phenoxy (C2 to C6) alkynylgroup”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry andRz represent, may have a straight chain, branch or ring. Examples of thesubstituent which may be substituted with a phenoxy group include ahalogen atom, a C1 to C4 alkyl group which may be substituted withhalogen, a C1 to C4 alkyloxy group which may be substituted withhalogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, amethoxy group, a nitro group, a cyano group and the like. Specificexamples thereof include a phenoxy group, a phenoxymethyl group, a2-phenoxyethyl group, a 2-phenoxyethenyl group, a 2-phenoxyethynylgroup, a 4-chlorophenoxy group, a 2-methylphenoxy group and the like,and preferred examples thereof include a 2-phenoxyethyl group.

The 5- to 10-membered heterocycle of “a substituted or unsubstituted 5-to 10-membered heterocycle, a substituted or unsubstituted 5- to10-membered heterocycle (C1 to C6) alkyl group, a substituted orunsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group anda substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6)alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7,Ry and Rz represent, represents a ring including a hetero atom, such asan oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting1 to 4 rings, and examples thereof include a furanyl group, a thienylgroup, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, apiperazinyl group, a pyrimidinyl group, a morpholinyl group, a triazolylgroup, an imidazolyl group, a triazolyl group, a tetrahydrofuranylgroup, a quinolinyl group and the like. Examples of the substituentwhich may be substituted with a heterocycle include a halogen atom, a C1to C4 alkyl group which may be substituted with halogen, a C1 to C4alkyloxy group which may be substituted with halogen, a C3 to C6 cyclicalkyl group, a methylsulfonyl group, a methoxy group, a nitro group, acyano group and the like. The (C1 to C6) alkyl group, (C2 to C6) alkenylgroup and (C2 to C6) alkenyl group may have a straight chain, branch orring. Specific examples thereof include a 2-pyridyl group, a 3-pyridylgroup, a 4-pyridyl group, a 2-pyridylmethyl group, a 3-pyridylmethylgroup, a 4-pyridylmethyl group, a 2-(4-pyridyl)ethenyl group, a2-(4-pyridyl)ethynyl group, a 2-furanylmethyl group, a 2-thienylmethylgroup, a 2-tetrahydrofuranylmethyl group and the like, and preferredexamples thereof include a 2-pyridylmethyl group, a 3-pyridylmethylgroup, a 4-pyridylmethyl group, a 2-furanylmethyl group, a2-thienylmethyl group and a 2-tetrahydrofuranylmethyl group.

The (C1 to C4) alkoxy of “a (C1 to C4) alkoxy (C1 to C5) alkyl group, a(C1 to C4) alkoxy (C2 to C5) alkenyl group and a (C1 to C4) alkoxy (C2to C5) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b,R6c, R6e, R6f, R7 and Rz represent, represents a (C1 to C4) alkyloxy,alkenyloxy and alkynyloxy having a straight chain, branch or ring.Specific examples thereof include a methoxymethyl group, a2-methoxyethyl group, an ethoxymethyl group, a 2-ethoxyethyl group, a3-methoxy-2-propenyl group, a 3-methoxy-2-propynyl group and the like.R4 is preferably a 2-methoxyethyl group.

The (C1 to C4) alkylthio of “a (C1 to C4) alkylthio (C1 to C5) alkylgroup, a (C1 to C4) alkylthio (C2 to C5) alkenyl group and a (C1 to C4)alkylthio (C2 to C5) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5,R6, R6a, R6b, R6c, R6e, R6f, R7 and Rz represent, represents a (C1 toC4) alkylthio, alkenylthio and alkynylthio having a straight chain,branch or ring. Examples thereof include a methylthiomethyl group, a2-methylthioethyl group, an ethylthiomethyl group, a 2-ethylthioethylgroup, a 3-methylthio-2-propenyl group, a 3-methylthio-2-propynyl groupand the like. R4 is preferably a 2-methylthioethyl group.

The (C6 to C10) aryl of “a substituted or unsubstituted (C6 to C10) arylgroup”, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6g, R6h, R6i, R6j andR6k represent, specifically represents a phenyl group and a naphthylgroup, and the (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2to C6) alkenyl group may have a straight chain, branch or ring. Examplesof the substituent which may be substituted with an aryl group include ahalogen atom, a C1 to C4 alkyl group which may be substituted withhalogen, a C1 to C4 alkyloxy group which may be substituted withhalogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, amethoxy group, a nitro group, a cyano group and the like. Specificexamples thereof include a phenyl group, a 2-methylphenyl group, a3-methoxyphenyl group, a 4-nitrophenyl group, a 4-cyanophenyl group andthe like.

The 5- to 10-membered heterocycle of “a substituted or unsubstituted 5-to 10-membered heterocycle”, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6gand R6h represent, represents a ring including a hetero atom, such as anoxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1to 4 rings, and examples thereof include a furanyl group, a thienylgroup, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, apiperazinyl group, a pyrimidinyl group, a morpholinyl group, a triazolylgroup, an imidazolyl group, a triazolyl group, a tetrahydrofuranylgroup, a quinolinyl group and the like. Examples of the substituentwhich may be substituted with a heterocycle include a halogen atom, a C1to C4 alkyl group which may be substituted with halogen, a C1 to C4alkyloxy group which may be substituted with halogen, a C3 to C6 cyclicalkyl group, a methylsulfonyl group, a methoxy group, a nitro group, acyano group and the like. Specific examples thereof include a 2-pyridylgroup, a 3-pyridyl group, a 4-pyridyl group, a 2-furanyl group, a2-thienyl group, a 2-tetrahydrofuranyl group and the like.

As a preferred aspect of a compound represented by Formula (I),

R represents the following Formula (a),

Ar represents a 6-chloro-3-pyridyl group, a 2-chloro-5-thiazolyl group,a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a6-bromo-3-pyridyl group, a 2-chloro-5-pyrimidinyl group, a6-trifluoromethyl-3-pyridyl group and a 2-chloro-5-pyrimidinyl group,

A represents a ring represented by A-1, A-13, A-14, A-15, A-16, A-23 andA-38,

Y represents a hydrogen atom and a 3-cyano group, and

R1 represents a trifluoromethyl group, a difluoromethyl group, achlorodifluoromethyl group, a pentafluoroethyl group, a trifluoroethylgroup, an ethenyl group and a 2-propynyl group.

As another preferred aspect of a compound represented by Formula (I),

R represents the following Formula (c),

Ar represents a 6-chloro-3-pyridyl group, a 2-chloro-5-thiazolyl group,a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a6-bromo-3-pyridyl group, a 2-chloro-5-pyrimidyl group and a6-trifluoromethyl-3-pyridyl group,

A represents a ring represented by A-1,

Y represents a hydrogen atom, and

R3 represents a trifluoromethyl group, a difluoromethyl group, achlorodifluoromethyl group and a pentafluoroethyl group.

As still another preferred aspect of a compound represented by Formula(I),

R represents the following Formula (d),

Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridylgroup, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a2-chloro-5-pyrimidyl group,

A represents a ring represented by A-1,

Y represents a hydrogen atom,

R4 represents a hydrogen atom, a methyl group, an ethyl group, ann-propyl group, an isopropyl group, a cyclopropyl group, a cyclobutylgroup, a cyclohexyl group, and cyclopentyl group, and

R5 represents a trifluoromethyl group, a difluoromethyl group, achlorodifluoromethyl group and a pentafluoroethyl group.

As yet another preferred aspect of a compound represented by Formula(I),

R represents the following Formula (e) group

Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridylgroup, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a2-chloro-5-pyrimidyl group,

A represents a ring represented by A-1,

Y represents a hydrogen atom, and

R6 represents a hydrogen atom, a methyl group, an ethyl group, a2-propenyl group, a methylcarbonyl group, an ethylcarbonyl group, acyclopropylcarbonyl group, an ethenylcarbonyl group, a2-propynylcarbonyl group, a benzoyl group, a 3-pyridylcarbonyl group, amethyloxycarbonyl group and a phenyloxycarbonyl group, and

R7 represents a trifluoromethyl group, a difluoromethyl group, achlorodifluoromethyl group and a pentafluoroethyl group.

Specific examples of the compound of Formula (I) include a compoundrepresented by a combination of the following Table A and Table B.

TABLE 1 Table A Compound No. Ar A Y R Table 1- 6-Chloro-3-pyridyl A-1 Hrepresents a 1 5~1- combination of 710 substituents corresponding toeach row of Nos. (1 and 6) below of Table B Table 2-2-Chloro-5-thiazolyl A-1 H represents a 2 1~2- combination of 710substituents corresponding to each row of Table B Table 3-6-Fluoro-3-pyridyl A-1 H represents a 3 2~3- combination of 710substituents corresponding to each row of Nos. (1 and 3) below of TableB Table 4- 6-Bromo-3-pyridyl A-1 H represents a 4 2~4- combination of710 substituents corresponding to each row of Nos. (1 and 3) below ofTable B Table 5- 6-Chloro-5-fluoro- A-1 H represents a 5 2~5- 3-pyridylcombination of 710 substituents corresponding to each row of Nos. (1 and3) below of Table B Table 6- 2-Chloro-5- A-1 H represents a 6 2~6-pyrimidinyl combination of 710 substituents corresponding to each row ofNos. (1 and 3) below of Table B Table 7- 5-Chloropyrazin- A-1 Hrepresents a 7 1~7- 2-yl combination of 710 substituents correspondingto each row of Table B Table 8- 6-Chloropyridazin- A-1 H represents a 81~8- 3-yl combination of 710 substituents corresponding to each row ofTable B Table 9- 2-Chloro-5-oxazolyl A-1 H represents a 9 1~9-combination of 710 substituents corresponding to each row of Table BTable 10- 6-trifluoromethyl- A-1 H represents a 10 1~10- 3-pyridylcombination of 710 substituents corresponding to each row of Table BTable 11- 3-tetrahydrofuranyl A-1 H represents a 11 1~11- combination of710 substituents corresponding to each row of Table B Table 12-2-Chloro-4-pyridyl A-1 H represents a 12 1~12- combination of 710substituents corresponding to each row of Table B Table 13-3-Cyanophenyl A-1 H represents a 13 1~13- combination of 710substituents corresponding to each row of Table B Table 14-6-Chloro-3-pyridyl A-1 3-F represents a 14 1~14- combination of 710substituents corresponding to each row of Table B Table 15-2-Chloro-5-thiazolyl A-1 3-F represents a 15 1~15- combination of 710substituents corresponding to each row of Table B Table 16-6-Fluoro-3-pyridyI A-1 3-F represents a 16 1~16- combination of 710substituents corresponding to each row of Table B Table 17-6-Bromo-3-pyridyl A-1 3-F represents a 17 1~17- combination of 710substituents corresponding to each row of Table B Table 18-6-Chloro-5-fluoro- A-1 3-F represents a 18 1~18- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 19-2-Chloro-5- A-1 3-F represents a 19 1~19- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 20-5-Chloropyrazin- A-1 3-F represents a 20 1~20- 2-yl combination of 710substituents corresponding to each row of Table B Table 21-6-Chloropyridazin- A-1 3-F represents a 21 1~21- 3-yl combination of 710substituents corresponding to each row of Table B Table 22-2-Chloro-5-oxazolyl A-1 3-F represents a 22 1~22- combination of 710substituents corresponding to each row of Table B Table 23-6-trifluoromethyl- A-1 3-F represents a 23 1~23- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 24-3-tetrahydrofuranyl A-1 3-F represents a 24 1~24- combination of 710substituents corresponding to each row of Table B Table 25-6-Chloro-3-pyridyl A-1 4-F represents a 25 1~25- combination of 710substituents corresponding to each row of Table B Table 26-2-Chloro-5-thiazolyl A-1 4-F represents a 26 1~26- combination of 710substituents corresponding to each row of Table B Table 27-6-Fluoro-3-pyridyl A-1 4-F represents a 27 1~27- combination of 710substituents corresponding to each row of Table B Table 28-6-Bromo-3-pyridyl A-1 4-F represents a 28 1~28- combination of 710substituents corresponding to each row of Table B Table 29-6-Chloro-5-fluoro- A-1 4-F represents a 29 1~29- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 30-2-Chloro-5- A-1 4-F represents a 30 1~30- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 31-5-Chloropyrazin- A-1 4-F represents a 31 1~31- 2-yl combination of 710substituents corresponding to each row of Table B Table 32-6-Chloropyridazin- A-1 4-F represents a 32 1~32- 3-yl combination of 710substituents corresponding to each row of Table B

TABLE 2 Table A Compound No. Ar A Y R Table 33- 2-Chloro-5-oxazolyl A-14-F represents a 33 1~33- combination of 710 substituents correspondingto each row of Table B Table 34- 6-trifluoromethyl- A-1 4-F represents a34 1~34- 3-pyridyl combination of 710 substituents corresponding to eachrow of Table B Table 35- 3-tetrahydrofuranyl A-1 4-F represents a 351~35- combination of 710 substituents corresponding to each row of TableB Table 36- 6-Chloro-3-pyridyl A-1 5-F represents a 36 1~36- combinationof 710 substituents corresponding to each row of Table B Table 37-2-Chloro-5-thiazolyl A-1 5-F represents a 37 1~37- combination of 710substituents corresponding to each row of Table B Table 38-6-Fluoro-3-pyridyl A-1 5-F represents a 38 1~38- combination of 710substituents corresponding to each row of Table B Table 39-6-Bromo-3-pyridyl A-1 5-F represents a 39 1~39- combination of 710substituents corresponding to each row of Table B Table 40-6-Chloro-5-fluoro- A-1 5-F represents a 40 1~40- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 41-2-Chloro-5- A-1 5-F represents a 41 1~41- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 42-5-Chloropyrazin- A-1 5-F represents a 42 1~42- 2-yl combination of 710substituents corresponding to each row of Table B Table 43-6-Chloropyridazin- A-1 5-F represents a 43 1~43- 3-yl combination of 710substituents corresponding to each row of Table B Table 44-2-Chloro-5-oxazolyl A-1 5-F represents a 44 1~44- combination of 710substituents corresponding to each row of Table B Table 45-6-trifluoromethyl- A-1 5-F represents a 45 1~45- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 46-3-tetrahydrofuranyl A-1 5-F represents a 46 1~46- combination of 710substituents corresponding to each row of Table B Table 47-6-Chloro-3-pyridyl A-1 6-F represents a 47 1~47- combination of 710substituents corresponding to each row of Table B Table 48-2-Chloro-5-thiazolyl A-1 6-F represents a 48 1~48- combination of 710substituents corresponding to each row of Table B Table 49-6-Fluoro-3-pyridyl A-1 6-F represents a 49 1~49- combination of 710substituents corresponding to each row of Table B Table 50-6-Bromo-3-pyridyl A-1 6-F represents a 50 1~50- combination of 710substituents corresponding to each row of Table B Table 51-6-Chloro-5-fluoro- A-1 6-F represents a 51 1~51- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 52-2-Chloro-5- A-1 6-F represents a 52 1~52- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 53-5-Chloropyrazin- A-1 6-F represents a 53 1~53- 2-yl combination of 710substituents corresponding to each row of Table B Table 54-6-Chloropyridazin- A-1 6-F represents a 54 1~54- 3-yl combination of 710substituents corresponding to each row of Table B Table 55-2-Chloro-5-oxazolyl A-1 6-F represents a 55 1~55- combination of 710substituents corresponding to each row of Table B Table 56-6-trifluoromethyl- A-1 6-F represents a 56 1~56- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 57-3-tetrahydrofuranyl A-1 6-F represents a 57 1~57- combination of 710substituents corresponding to each row of Table B Table 58-6-Chloro-3-pyridyl A-1 3-Cl represents a 58 1~58- combination of 710substituents corresponding to each row of Table B Table 59-2-Chloro-5-thiazolyl A-1 3-Cl represents a 59 1~59- combination of 710substituents corresponding to each row of Table B Table 60-6-Fluoro-3-pyridyl A-1 3-Cl represents a 60 1~60- combination of 710substituents corresponding to each row of Table B Table 61-6-Bromo-3-pyridyl A-1 3-Cl represents a 61 1~61- combination of 710substituents corresponding to each row of Table B Table 62-6-Chloro-5-fluoro- A-1 3-Cl represents a 62 1~62- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 63-2-Chloro-5- A-1 3-Cl represents a 63 1~63- pyrimidinyl combination of642 substituents corresponding to each row of Table B Table 64-5-Chloropyrazin- A-1 3-Cl represents a 64 1~64- 2-yl combination of 710substituents corresponding to each row of Table B

TABLE 3 Table A Compound No. Ar A Y R Table 65- 6- A-1 3- represents a65 1~65- Chloropyridazin- Cl combination of 710 3-yl substituentscorresponding to each row of Table B Table 66- 2-Chloro-5- A-1 3-represents a 66 1~66- oxazolyl Cl combination of 710 substituentscorresponding to each row of Table B Table 67- 6- A-1 3- represents a 671~67- trifluoromethyl- Cl combination of 710 3-pyridyl substituentscorresponding to each row of Table B Table 68- 3- A-1 3- represents a 681~68- tetrahydrofuranyl Cl combination of 710 substituents correspondingto each row of Table B Table 69- 6-Chloro-3- A-1 4- represents a 691~69- pyridyl Cl combination of 710 substituents corresponding to eachrow of Table B Table 70- 2-Chloro-5- A-1 4- represents a 70 1~70-thiazolyl Cl combination of 710 substituents corresponding to each rowof Table B Table 71- 6-Fluoro-3- A-1 4- represents a 71 1~71- pyridyl Clcombination of 710 substituents corresponding to each row of Table BTable 72- 6-Bromo-3- A-1 4- represents a 72 1~72- pyridyl Cl combinationof 710 substituents corresponding to each row of Table B Table 73-6-Chloro-5- A-1 4- represents a 73 1~73- fluoro-3- Cl combination of 710pyridyl substituents corresponding to each row of Table B Table 74-2-Chloro-5- A-1 4- represents a 74 1~74- pyrimidinyl Cl combination of710 substituents corresponding to each row of Table B Table 75- 5- A-14- represents a 75 1~75- Chloropyrazin- Cl combination of 710 2-ylsubstituents corresponding to each row of Table B Table 76- 6- A-1 4-represents a 76 1~76- Chloropyridazin- Cl combination of 710 3-ylsubstituents corresponding to each row of Table B Table 77- 2-Chloro-5-A-1 4- represents a 77 1~77- oxazolyl Cl combination of 710 substituentscorresponding to each row of Table B Table 78- 6- A-1 4- represents a 781~78- trifluoromethyI- Cl combination of 710 3-pyridyI substituentscorresponding to each row of Table B Table 79- 3- A-1 4- represents a 791~79- tetrahydrofuranyl Cl combination of 710 substituents correspondingto each row of Table B Table 80- 6-Chloro-3- A-1 5- represents a 801~80- pyridyl Cl combination of 710 substituents corresponding to eachrow of Table B Table 81- 2-Chloro-5- A-1 5- represents a 81 1~81-thiazolyl Cl combination of 710 substituents corresponding to each rowof Table B Table 82- 6-Fluoro-3- A-1 5- represents a 82 1~82- pyridyl Clcombination of 710 substituents corresponding to each row of Table BTable 83- 6-Bromo-3- A-1 5- represents a 83 1~83- pyridyl Cl combinationof 710 substituents corresponding to each row of Table B Table 84-6-Chloro-5- A-1 5- represents a 84 1~84- fluoro-3- Cl combination of 710pyridyl substituents corresponding to each row of Table B Table 85-2-Chloro-5- A-1 5- represents a 85 1~85- pyrimidinyl Cl combination of710 substituents corresponding to each row of Table B Table 86- 5- A-15- represents a 86 1~86- Chloropyrazin- Cl combination of 710 2-ylsubstituents corresponding to each row of Table B Table 87- 6- A-1 5-represents a 87 1~87- Chloropyridazin- Cl combination of 710 3-ylsubstituents corresponding to each row of Table B Table 88- 2-Chloro-5-A-1 5- represents a 88 1~88- oxazolyl Cl combination of 710 substituentscorresponding to each row of Table B Table 89-1~89- 6- A-1 5- representsa 89 710 trifluoromethyl- Cl combination of 3-pyridyl substituentscorresponding to each row of Table B Table 90- 3- A-1 5- represents a 901~90- tetrahydrofuranyl Cl combination of 710 substituents correspondingto each row of Table B Table 91- 6-Chloro-3- A-1 6- represents a 911~91- pyridyl Cl combination of 710 substituents corresponding to eachrow of Table B Table 92- 2-Chloro-5- A-1 6- represents a 92 1~92-thiazolyl Cl combination of 710 substituents corresponding to each rowof Table B Table 93- 6-Fluoro-3- A-1 6- represents a 93 1~93- pyridyl Clcombination of 710 substituents corresponding to each row of Table BTable 94- 6-Bromo-3- A-1 6- represents a 94 1~94- pyridyl Cl combinationof 710 substituents corresponding to each row of Table B Table 95-6-Chloro-5- A-1 6- represents a 95 1~95- fluoro-3- Cl combination of 710pyridyl substituents corresponding to each row of Table B Table 96-2-Chloro-5- A-1 6- represents a 96 1~96- pyrimidinyl Cl combination of710 substituents corresponding to each row of Table B

TABLE 4 Table A Compound No. Ar A Y R Table 97- 5- A-1 6- represents a97 1~97- Chloropyrazin- Cl combination of 710 2-yl substituentscorresponding to each row of Table B Table 98- 6- A-1 6- represents a 981~98- Chloropyridazin- Cl combination of 710 3-yl substituentscorresponding to each row of Table B Table 99- 2-Chloro-5- A-1 6-represents a 99 1~99- oxazolyl Cl combination of 710 substituentscorresponding to each row of Table B Table 100- 6- A-1 6- represents a100 1~100- trifluoromethyI- Cl combination of 710 3-pyridyl substituentscorresponding to each row of Table B Table 101- 3- A-1 6- represents a101 1~101- tetrahydrofuranyl Cl combination of 710 substituentscorresponding to each row of Table B Table 102- 6-Chloro-3- A-1 3-represents a 102 1~102- pyridyl CN combination of 710 substituentscorresponding to each row of Table B Table 103- 2-Chloro-5- A-1 3-represents a 103 1~103- thiazolyl CN combination of 710 substituentscorresponding to each row of Table B Table 104- 6-Fluoro-3- A-1 3-represents a 104 1~104- pyridyl CN combination of 710 substituentscorresponding to each row of Table B Table 105- 6-Bromo-3- A-1 3-represents a 105 1~105- pyridyl CN combination of 710 substituentscorresponding to each row of Table B Table 106- 6-Chloro-5- A-1 3-represents a 106 1~106- fluoro-3- CN combination of 710 pyridylsubstituents corresponding to each row of Table B Table 107- 2-Chloro-5-A-1 3- represents a 107 1~107- pyrimidinyl CN combination of 710substituents corresponding to each row of Table B Table 108- 5- A-1 3-represents a 108 1~108- Chloropyrazin- CN combination of 710 2-ylsubstituents corresponding to each row of Table B Table 109- 6- A-1 3-represents a 109 1~109- Chloropyridazin- CN combination of 710 3-ylsubstituents corresponding to each row of Table B Table 110- 2-Chloro-5-A-1 3- represents a 110 1~110- oxazolyl CN combination of 710substituents corresponding to each row of Table B Table 111- 6- A-1 3-represents a 111 1~111- trifluoromethyl- CN combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 112- 3- A-1 3-represents a 112 1~112- tetrahydrofuranyl CN combination of 710substituents corresponding to each row of Table B Table 113- 6-Chloro-3-A-1 4- represents a 113 1~113- pyridyl CN combination of 710substituents corresponding to each row of Table B Table 114- 2-Chloro-5-A-1 4- represents a 114 1~114- thiazolyl CN combination of 710substituents corresponding to each row of Table B Table 115- 6-Fluoro-3-A-1 4- represents a 115 1~115- pyridyl CN combination of 710substituents corresponding to each row of Table B Table 116- 6-Bromo-3-A-1 4- represents a 116 1~116- pyridyl CN combination of 710substituents corresponding to each row of Table B Table 117- 6-Chloro-5-A-1 4- represents a 117 1~117- Fluoro-3- CN combination of 710 pyridylsubstituents corresponding to each row of Table B Table 118- 2-Chloro-5-A-1 4- represents a 118 1~118- pyrimidinyl CN combination of 710substituents corresponding to each row of Table B Table 119- 5- A-1 4-represents a 119 1~119- Chloropyrazin- CN combination of 710 2-ylsubstituents corresponding to each row of Table B Table 120- 6- A-1 4-represents a 120 1~120- Chloropyridazin- CN combination of 710 3-ylsubstituents corresponding to each row of Table B Table 121- 2-Chloro-5-A-1 4- represents a 121 1~121- oxazolyl CN combination of 710substituents corresponding to each row of Table B Table 122- 6- A-1 4-represents a 122 1~122- trifluoromethyl- CN combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 123- 3- A-1 4-represents a 123 1~123- tetrahydrofuranyl CN combination of 710substituents corresponding to each row of Table B Table 124- 6-Chloro-3-A-1 5- represents a 124 1~124- pyridyl CN combination of 710substituents corresponding to each row of Table B Table 125- 2-Chloro-5-A-1 5- represents a 125 1~155- thiazolyl CN combination of 710substituents corresponding to each row of Table B Table 126- 6-Fluoro-3-A-1 5- represents a 126 1~126- pyridyl CN combination of 710substituents corresponding to each row of Table B Table 127- 6-Bromo-3-A-1 5- represents a 127 1~127- pyridyl CN combination of 710substituents corresponding to each row of Table B Table 128- 6-Chloro-5-A-1 5- represents a 128 1~128- fluoro-3- CN combination of 710 pyridylsubstituents corresponding to each row of Table B

TABLE 5 Table A Compound No. Ar A Y R Table 129- 2-Chloro-5- A-1 5-represents a 129 1~129- pyrimidinyl CN combination of 710 substituentscorresponding to each row of Table B Table 130- 5- A-1 5- represents a130 1~130- Chloropyrazin- CN combination of 710 2-yl substituentscorresponding to each row of Table B Table 131- 6- A-1 5- represents a131 1~131- Chloropyridazin- CN combination of 710 3-yl substituentscorresponding to each row of Table B Table 132- 2-Chloro-5- A-1 5-represents a 132 1~132- oxazolyl CN combination of 710 substituentscorresponding to each row of Table B Table 133- 6- A-1 5- represents a133 1~133- trifluoromethyl- CN combination of 710 3-pyridyl substituentscorresponding to each row of Table B Table 134- 3- A-1 5- represents a134 1~134- tetrahydrofuranyl CN combination of 710 substituentscorresponding to each row of Table B Table 135- 6-Chloro-3- A-1 6-represents a 135 1~135- pyridyl CN combination of 710 substituentscorresponding to each row of Table B Table 136- 2-Chloro-5- A-1 6-represents a 136 1~136- thiazolyl CN combination of 710 substituentscorresponding to each row of Table B Table 137- 6-Fluoro-3- A-1 6-represents a 137 1~137- pyridyl CN combination of 710 substituentscorresponding to each row of Table B Table 138- 6-Bromo-3- A-1 6-represents a 138 1~138- pyridyl CN combination of 710 substituentscorresponding to each row of Table B Table 139- 6-Chloro-5- A-1 6-represents a 139 1~139- fluoro-3- CN combination of 710 pyridylsubstituents corresponding to each row of Table B Table 140-1~140-2-Chloro-5- A-1 6- represents a 140 710 pyrimidinyl CN combination ofsubstituents corresponding to each row of Table B Table 141- 5- A-1 6-represents a 141 1~141- Chloropyrazin- CN combination of 710 2-ylsubstituents corresponding to each row of Table B Table 142- 6- A-1 6-represents a 142 1~142- Chloropyridazin- CN combination of 710 3-ylsubstituents corresponding to each row of Table B Table 143- 2-Chloro-5-A-1 6- represents a 143 1~143- oxazolyl CN combination of 710substituents corresponding to each row of Table B Table 144- 6- A-1 6-represents a 144 1~144- trifluoromethyl- CN combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 145- 3- A-1 6-represents a 145 1~145- tetrahydrofuranyl CN combination of 710substituents corresponding to each row of Table B Table 146- 6-Chloro-3-A-1 3- represents a 146 1~146- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 147- 2-Chloro-5-A-1 3- represents a 147 1~147- thiazolyl OH combination of 710substituents corresponding to each row of Table B Table 148- 6-Fluoro-3-A-1 3- represents a 148 1~148- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 149- 6-Bromo-3-A-1 3- represents a 149 1~149- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 150- 6-Chloro-5-A-1 3- represents a 150 1~150- Fluoro-3- OH combination of 710 pyridylsubstituents corresponding to each row of Table B Table 151- 2-Chloro-5-A-1 3- represents a 151 1~151- pyrimidinyl OH combination of 710substituents corresponding to each row of Table B Table 152- 5- A-1 3-represents a 152 1~152- Chloropyrazin- OH combination of 710 2-ylsubstituents corresponding to each row of Table B Table 153- 6- A-1 3-represents a 153 1~153- Chloropyridazin- OH combination of 710 3-ylsubstituents corresponding to each row of Table B Table 154- 2-Chloro-5-A-1 3- represents a 154 1~154- oxazolyl OH combination of 710substituents corresponding to each row of Table B Table 155- 6- A-1 3-represents a 155 1~155- trifluoromethyl- OH combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 156- 3- A-1 3-represents a 156 1~156- tetrahydrofuranyl OH combination of 710substituents corresponding to each row of Table B Table 157- 6-Chloro-3-A-1 4- represents a 157 1~157- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 158- 2-Chloro-5-A-1 4- represents a 158 1~158- thiazolyl OH combination of 710substituents corresponding to each row of Table B Table 159- 6-Fluoro-3-A-1 4- represents a 159 1~159- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 160- 6-Bromo-3-A-1 4- represents a 160 1~160- pyridyl OH combination of 710substituents corresponding to each row of Table B

TABLE 6 Table A Compound No. Ar A Y R Table 161- 6-Chloro-5- A-1 4-represents a 161 1~161- fluoro-3- OH combination of 710 pyridylsubstituents corresponding to each row of Table B Table 162- 2-Chloro-5-A-1 4- represents a 162 1~162- pyrimidinyl OH combination of 710substituents corresponding to each row of Table B Table 163- 5- A-1 4-represents a 163 1~163- Chloropyrazin- OH combination of 710 2-ylsubstituents corresponding to each row of Table B Table 164- 6- A-1 4-represents a 164 1~164- Chloropyridazin- OH combination of 710 3-ylsubstituents corresponding to each row of Table B Table 165- 2-Chloro-5-A-1 4- represents a 165 1~165- oxazolyl OH combination of 710substituents corresponding to each row of Table B Table 166- 6- A-1 4-represents a 166 1~166- trifluoromethyl- OH combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 167- 3- A-1 4-represents a 167 1~167- tetrahydrofuranyl OH combination of 710substituents corresponding to each row of Table B Table 168- 6-Chloro-3-A-1 5- represents a 168 1~168- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 169- 2-Chloro-5-A-1 5- represents a 169 1~169- thiazolyl OH combination of 710substituents corresponding to each row of Table B Table 170- 6-Fluoro-3-A-1 5- represents a 170 1~170- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 171- 6-Bromo-3-A-1 5- represents a 171 1~171- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 172- 6-Chloro-5-A-1 5- represents a 172 1~172- fluoro-3- OH combination of 710 pyridylsubstituents corresponding to each row of Table B Table 173- 2-Chloro-5-A-1 5- represents a 173 1~173- pyrimidinyl OH combination of 710substituents corresponding to each row of Table B Table 174- 5- A-1 5-represents a 174 1~174- Chloropyrazin- OH combination of 710 2-ylsubstituents corresponding to each row of Table B Table 175- 6- A-1 5-represents a 175 1~175- Chloropyridazin- OH combination of 710 3-ylsubstituents corresponding to each row of Table B Table 176- 2-Chloro-5-A-1 5- represents a 176 1~176- oxazolyl OH combination of 710substituents corresponding to each row of Table B Table 177- 6- A-1 5-represents a 177 1~177- trifluoromethyl- OH combination of 710 3-pyridyIsubstituents corresponding to each row of Table B Table 178- 3- A-1 5-represents a 178 1~178- tetrahydrofuranyl OH combination of 710substituents corresponding to each row of Table B Table 179- 6-Chloro-3-A-1 6- represents a 179 1~179- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 180- 2-Chloro-5-A-1 6- represents a 180 1~180- thiazolyl OH combination of 710substituents corresponding to each row of Table B Table 181- 6-Fluoro-3-A-1 6- represents a 181 1~181- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 182- 6-Bromo-3-A-1 6- represents a 182 1~182- pyridyl OH combination of 710substituents corresponding to each row of Table B Table 183- 6-Chloro-5-A-1 6- represents a 183 1~183- fluoro-3- OH combination of 710 pyridylsubstituents corresponding to each row of Table B Table 184- 2-Chloro-5-A-1 6- represents a 184 1~184- pyrimidinyl OH combination of 710substituents corresponding to each row of Table B Table 185- 5- A-1 6-represents a 185 1~185- Chloropyrazin- OH combination of 710 2-ylsubstituents corresponding to each row of Table B Table 186- 6- A-1 6-represents a 186 1~186- Chloropyridazin- OH combination of 710 3-ylsubstituents corresponding to each row of Table B Table 187- 2-Chloro-5-A-1 6- represents a 187 1~187- oxazolyl OH combination of 710substituents corresponding to each row of Table B Table 188- 6- A-1 6-represents a 188 1~188- trifluoromethyl- OH combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 189- 3- A-1 6-represents a 189 1~189- tetrahydrofuranyl OH combination of 710substituents corresponding to each row of Table B Table 190- 6-Chloro-3-A- H represents a 190 1~190- pyridyl 13 combination of 710 substituentscorresponding to each row of Table B Table 191- 2-Chloro-5- A- Hrepresents a 191 1~191- thiazolyl 13 combination of 710 substituentscorresponding to each row of Table B Table 192- 6-Fluoro-3- A- Hrepresents a 192 1~192- pyridyl 13 combination of 710 substituentscorresponding to each row of Table B

TABLE 7 Table A Compound No. Ar A Y R Table 193- 6-Bromo-3- A-13 Hrepresents a 193 1~193- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 194- 6-Chloro-5- A-13 Hrepresents a 194 1~194- fluoro-3- combination of 710 pyridylsubstituents corresponding to each row of Table B Table 195- 2-Chloro-5-A-13 H represents a 195 1~195- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 196-5-Chloropyrazin- A-13 H represents a 196 1~196- 2-yl combination of 710substituents corresponding to each row of Table B Table 197-6-Chloropyridazin- A-13 H represents a 197 1~197- 3-yl combination of710 substituents corresponding to each row of Table B Table 198-2-Chloro-5- A-13 H represents a 198 1~198- oxazolyl combination of 710substituents corresponding to each row of Table B Table 199-6-trifluoromethyl- A-13 H represents a 199 1~199- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 200- 3-A-13 H represents a 200 1~200- tetrahydrofuranyl combination of 710substituents corresponding to each row of Table B Table 201- 6-Chloro-3-A-14 H represents a 201 1~201- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 202- 2-Chloro-5- A-14 Hrepresents a 202 1~202- thiazolyl combination of 710 substituentscorresponding to each row of Table B Table 203- 6-Fluoro-3- A-14 Hrepresents a 203 1~203- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 204- 6-Bromo-3- A-14 Hrepresents a 204 1~204- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 205- 6-Chloro-5- A-14 Hrepresents a 205 1~205- fluoro-3- combination of 710 pyridylsubstituents corresponding to each row of Table B Table 206- 2-Chloro-5-A-14 H represents a 206 1~206- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 207-5-Chloropyrazin- A-14 H represents a 207 1~207- 2-yl combination of 710substituents corresponding to each row of Table B Table 208-6-Chloropyridazin- A-14 H represents a 208 1~208- 3-yl combination of710 substituents corresponding to each row of Table B Table 209-2-Chloro-5- A-14 H represents a 209 1~209- oxazolyl combination of 710substituents corresponding to each row of Table B Table 210-6-trifluoromethyl- A-14 H represents a 210 1~210- 3-pyridyl combinationof 710 substituents corresponding to each row of Table B Table 211-3-tetrahydrofuranyl A-14 H represents a 211 1~211- combination of 710substituents corresponding to each row of Table B Table 212- 6-Chloro-3-A-15 H represents a 212 1~212- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 213- 2-Chloro-5- A-15 Hrepresents a 213 1~213- thiazolyl combination of 710 substituentscorresponding to each row of Table B Table 214- 6-Fluoro-3- A-15 Hrepresents a 214 1~214- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 215- 6-Bromo-3- A-15 Hrepresents a 215 1~215- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 216- 6-Chloro-5- A-15 Hrepresents a 216 1~216- fluoro-3- combination of 710 pyridylsubstituents corresponding to each row of Table B Table 217- 2-Chloro-5-A-15 H represents a 217 1~217- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 218- 5- A-15 Hrepresents a 218 1~218- Chloropyrazin combination of 710 -2-ylsubstituents corresponding to each row of Table B Table 219- 6- A-15 Hrepresents a 219 1~219- Chloropyridazin- combination of 710 3-ylsubstituents corresponding to each row of Table B Table 220- 2-Chloro-5-A-15 H represents a 220 1~220- oxazolyl combination of 710 substituentscorresponding to each row of Table B Table 221- 6- A-15 H represents a221 1~221- trifluoromethyl- combination of 710 3-pyridyl substituentscorresponding to each row of Table B Table 222- 3- A-15 H represents a222 1~222- tetrahydrofuranyl combination of 710 substituentscorresponding to each row of Table B Table 223- 6-Chloro-3- A-16 Hrepresents a 223 1~223- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 224- 2 -Chloro-5- A-16 Hrepresents a 224 1~224- thiazolyl combination of 710 substituentscorresponding to each row of Table B

TABLE 8 Table A Compound No. Ar A Y R Table 225- 6-Fluoro-3- A-16 Hrepresents a 225 1~225- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 226- 6-Bromo-3- A-16 Hrepresents a 226 1~226- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 227- 6-Chloro-5- A-16 Hrepresents a 227 1~227- fluoro-3- combination of 710 pyridylsubstituents corresponding to each row of Table B Table 228- 2-Chloro-5-A-16 H represents a 228 1~228- pyrimidinyl combination of 710substituents corresponding to each row of Table B Table 229- 5- A-16 Hrepresents a 229 1~229- Chloropyrazin- combination of 710 2-ylsubstituents corresponding to each row of Table B Table 230- 6- A-16 Hrepresents a 230 1~230- Chloropyridazin- combination of 710 3-ylsubstituents corresponding to each row of Table B Table 231- 2-Chloro-5-A-16 H represents a 231 1~231- oxazolyl combination of 710 substituentscorresponding to each row of Table B Table 232- 6- A-16 H represents a232 1~232- trifluoromethyl- combination of 710 3-pyridyl substituentscorresponding to each row of Table B Table 233- 3- A-16 H represents a233 1~233- tetrahydrofuranyl combination of 710 substituentscorresponding to each row of Table B Table 234- 6-Chloro-3- A-2 Hrepresents a 234 1~234- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 235- 6-Chloro-3- A-3 Hrepresents a 235 1~235- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 236- 6-Chloro-3- A-4 Hrepresents a 236 1~236- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 237- 6-Chloro-3- A-5 Hrepresents a 237 1~237- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 238- 6-Chloro-3- A-6 Hrepresents a 238 1~238- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 239- 6-Chloro-3- A-7 Hrepresents a 239 1~239- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 240- 6-Chloro-3- A-8 Hrepresents a 240 1~240- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 241- 6-Chloro-3- A-9 Hrepresents a 241 1~241- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 242- 6-Chloro-3- A-10 Hrepresents a 242 1~242- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 243- 6-Chloro-3- A-11 Hrepresents a 243 1~243- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 244- 6-Chloro-3- A-12 Hrepresents a 244 1~244- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 245- 6-Chloro-3- A-17 Hrepresents a 245 1~245- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 246- 6-Chloro-3- A-18 Hrepresents a 246 1~246- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 247- 6-Chloro-3- A-19 Hrepresents a 247 1~247- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 248- 6-Chloro-3- A-20 Hrepresents a 248 1~248- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 249- 6-Chloro-3- A-21 Hrepresents a 249 1~249- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 250- 6-Chloro-3- A-22 Hrepresents a 250 1~250- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 251- 6-Chloro-3- A-23 Hrepresents a 251 1~251- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 252- 6-Chloro-3- A-24 Hrepresents a 252 1~252- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 253- 6-Chloro-3- A-25 Hrepresents a 253 1~253- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 254- 6-Chloro-3- A-26 Hrepresents a 254 1~254- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 255- 6-Chloro-3- A-27 Hrepresents a 255 1~255- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 256- 6-Chloro-3- A-28 Hrepresents a 256 1~256- pyridyl combination of 710 substituentscorresponding to each row of Table B

TABLE 9 Table A Compound No. Ar A Y R Table 257- 6-Chloro-3- A-29 Hrepresents a 257 1~257- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 258- 6-Chloro-3- A-30 Hrepresents a 258 1~258- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 259- 6-Chloro-3- A-31 Hrepresents a 259 1~259- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 260- 6-Chloro-3- A-32 Hrepresents a 260 1~260- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 261- 6-Chloro-3- A-33 Hrepresents a 261 1~261- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 262- 6-Chloro-3- A-34 Hrepresents a 262 1~262- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 263- 6-Chloro-3- A-35 Hrepresents a 263 1~263- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 264- 6-Chloro-3- A-36 Hrepresents a 264 1~264- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 265- 6-Chloro-3- A-37 Hrepresents a 265 1~265- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 266- 6-Chloro-3- A-38 Hrepresents a 266 1~266- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 267- 6-Chloro-3- A-39 Hrepresents a 267 1~267- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 268- 6-Chloro-3- A-40 Hrepresents a 268 1~268- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 269- 6-Chloro-3- A-2 Hrepresents a 269 1~269- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 270- 6-Chloro-3- A-3 Hrepresents a 270 1~270- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 271- 6-Chloro-3- A-4 Hrepresents a 271 1~271- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 272- 6-Chloro-3- A-5 Hrepresents a 272 1~272- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 273- 6-Chloro-3- A-6 Hrepresents a 273 1~273- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 274- 6-Chloro-3- A-7 Hrepresents a 274 1~274- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 275- 6-Chloro-3- A-8 Hrepresents a 275 1~275- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 276- 6-Chloro-3- A-9 Hrepresents a 276 1~276- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 277- 6-Chloro-3- A-10 Hrepresents a 277 1~277- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 278- 6-Chloro-3- A-11 Hrepresents a 278 1~278- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 279- 6-Chloro-3- A-12 Hrepresents a 279 1~279- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 280- 6-Chloro-3- A-17 Hrepresents a 280 1~280- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 281- 6-Chloro-3- A-18 Hrepresents a 281 1~281- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 282- 6-Chloro-3- A-19 Hrepresents a 282 1~282- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 283- 6-Chloro-3- A-20 Hrepresents a 283 1~283- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 284- 6-Chloro-3- A-21 Hrepresents a 284 1~284- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 285- 6-Chloro-3- A-22 Hrepresents a 285 1~285- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 286- 6-Chloro-3- A-23 Hrepresents a 286 1~286- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 287- 6-Chloro-3- A-24 Hrepresents a 287 1~287- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 288- 6-Chloro-3- A-25 Hrepresents a 288 1~288- pyridyl combination of 710 substituentscorresponding to each row of Table B

TABLE 10 Table A Compound No. Ar A Y R Table 289- 6-Chloro-3- A-26 Hrepresents a 289 1~289- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 290- 6-Chloro-3- A-27 Hrepresents a 290 1~290- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 291- 6-Chloro-3- A-28 Hrepresents a 291 1~291- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 292- 6-Chloro-3- A-29 Hrepresents a 292 1~292- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 293- 6-Chloro-3- A-30 Hrepresents a 293 1~293- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 294- 6-Chloro-3- A-31 Hrepresents a 294 1~294- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 295- 6-Chloro-3- A-32 Hrepresents a 295 1~295- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 296- 6-Chloro-3- A-33 Hrepresents a 296 1~296- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 297- 6-Chloro-3- A-34 Hrepresents a 297 1~297- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 298- 6-Chloro-3- A-35 Hrepresents a 298 1~298- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 299- 6-Chloro-3- A-36 Hrepresents a 299 1~299- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 300- 6-Chloro-3- A-37 Hrepresents a 300 1~300- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 301- 6-Chloro-3- A-38 Hrepresents a 301 1~301- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 302- 6-Chloro-3- A-39 Hrepresents a 302 1~302- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 303- 6-Chloro-3- A-40 Hrepresents a 303 1~303- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 304- 6-Chloro-3- A-2 Hrepresents a 304 1~304- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 305- 6-Chloro-3- A-3 Hrepresents a 305 1~305- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 306- 6-Chloro-3- A-4 Hrepresents a 306 1~306- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 307- 6-Chloro-3- A-5 Hrepresents a 307 1~307- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 308- 6-Chloro-3- A-6 Hrepresents a 308 1~308- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 309- 6-Chloro-3- A-7 Hrepresents a 309 1~309- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 310- 6-Chloro-3- A-8 Hrepresents a 310 1~310- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 311- 6-Chloro-3- A-9 Hrepresents a 311 1~311- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 312- 6-Chloro-3- A-10 Hrepresents a 312 1~312- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 313- 6-Chloro-3- A-11 Hrepresents a 313 1~313- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 314- 6-Chloro-3- A-12 Hrepresents a 314 1~314- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 315- 6-Chloro-3- A-17 Hrepresents a 315 1~315- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 316- 6-Chloro-3- A-18 Hrepresents a 316 1~316- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 317- 6-Chloro-3- A-19 Hrepresents a 317 1~317- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 318- 6-Chloro-3- A-20 Hrepresents a 318 1~318- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 319- 6-Chloro-3- A-21 Hrepresents a 319 1~319- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 320- 6-Chloro-3- A-22 Hrepresents a 320 1~320- pyridyl combination of 710 substituentscorresponding to each row of Table B

TABLE 11 Table A Compound No Ar A Y R Table 321- 6-Chloro-3- A-23 Hrepresents a 321 1~321- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 322- 6-Chloro-3- A-24 Hrepresents a 322 1~322- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 323- 6-Chloro-3- A-25 Hrepresents a 323 1~323- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 324- 6-Chloro-3- A-26 Hrepresents a 324 1~324- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 325- 6-Chloro-3- A-27 Hrepresents a 325 1~325- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 326- 6-Chloro-3- A-28 Hrepresents a 326 1~326- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 327- 6-Chloro-3- A-29 Hrepresents a 327 1~327- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 328- 6-Chloro-3- A-30 Hrepresents a 328 1~328- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 329- 6-Chloro-3- A-31 Hrepresents a 329 1~329- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 330- 6-Chloro-3- A-32 Hrepresents a 330 1~330- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 331- 6-Chloro-3- A-33 Hrepresents a 331 1~331- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 332- 6-Chloro-3- A-34 Hrepresents a 332 1~332- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 333- 6-Chloro-3- A-35 Hrepresents a 333 1~333- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 334- 6-Chloro-3- A-36 Hrepresents a 334 1~334- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 335- 6-Chloro-3- A-37 Hrepresents a 335 1~335- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 336- 6-Chloro-3- A-38 Hrepresents a 336 1~336- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 337- 6-Chloro-3- A-39 Hrepresents a 337 1~337- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 338- 6-Chloro-3- A-40 Hrepresents a 338 1~338- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 339- 2-Chloro-5- A-2 Hrepresents a 339 1~339- thiazolyl combination of 710 substituentscorresponding to each row of Table B Table 340- 3- A-3 H represents a340 1~340- Trifluorometh combination of 710 ylphenyl substituentscorresponding to each row of Table B Table 341- 2- A-4 H represents a341 1~341- Methylphenyl combination of 710 substituents corresponding toeach row of Table B Table 342- 3- A-5 H represents a 342 1~342-Methylphenyl combination of 710 substituents corresponding to each rowof Table B Table 343- 4- A-6 H represents a 343 1~343- Methylphenylcombination of 710 substituents corresponding to each row of Table BTable 344- 4- A-7 H represents a 344 1~344- Trifluorometh combination of710 ylphenyl substituents corresponding to each row of Table B Table345- 2- A-8 H represents a 345 1~345- Trifluorometh combination of 710ylphenyl substituents corresponding to each row of Table B Table 346- 2-A-9 H represents a 346 1~346- Methoxyphenyl combination of 710substituents corresponding to each row of Table B Table 347- 3- A-10 Hrepresents a 347 1~347- Methoxyphenyl combination of 710 substituentscorresponding to each row of Table B Table 348- 4- A-11 H represents a348 1~348- Methoxyphenyl combination of 710 substituents correspondingto each row of Table B Table 349- 2-Cyanophenyl A-12 H represents a 3491~349- combination of 710 substituents corresponding to each row ofTable B Table 350- 3-Cyanophenyl A-17 H represents a 350 1~350-combination of 710 substituents corresponding to each row of Table BTable 351- 4-Cyanophenyl A-18 H represents a 351 1~351- combination of710 substituents corresponding to each row of Table B Table 352-2-Nitrophenyl A-19 H represents a 352 1~352- combination of 710substituents corresponding to each row of Table B

TABLE 12 Table A Compound No Ar A Y R Table 353- 3-Nitrophenyl A-20 Hrepresents a 353 1~353- combination of 710 substituents corresponding toeach row of Table B Table 354- 4-Nitrophenyl A-21 H represents a 3541~354- combination of 710 substituents corresponding to each row ofTable B Table 355- 3-Hydroxy-2- A-22 H represents a 355 1~355- pyridylcombination of 710 substituents corresponding to each row of Table BTable 356- 4-hydroxy-2- A-23 H represents a 356 1~356- pyridylcombination of 710 substituents corresponding to each row of Table BTable 357- 5-hydroxy-2- A-24 H represents a 357 1~357- pyridylcombination of 710 substituents corresponding to each row of Table BTable 358- 6-hydroxy-2- A-25 H represents a 358 1~358- pyridylcombination of 710 substituents corresponding to each row of Table BTable 359- 2-Hydroxy-3- A-26 H represents a 359 1~359- pyridylcombination of 710 substituents corresponding to each row of Table BTable 360- 5-Hydroxy-3- A-27 H represents a 360 1~360- pyridylcombination of 710 substituents corresponding to each row of Table BTable 361- 6-Hydroxy-3- A-28 H represents a 361 1~361- pyridylcombination of 710 substituents corresponding to each row of Table BTable 362- 4-Hydroxy-3- A-29 H represents a 362 1~362- pyridylcombination of 710 substituents corresponding to each row of Table BTable 363- 2-Hydroxy-4- A-30 H represents a 363 1~363- pyridylcombination of 710 substituents corresponding to each row of Table BTable 364- 3-Hydroxy-4- A-31 H represents a 364 1~364- pyridylcombination of 710 substituents corresponding to each row of Table BTable 365- 3-Chloro-2- A-32 H represents a 365 1~365- pyridylcombination of 710 substituents corresponding to each row of Table BTable 366- 4-Chloro-2- A-33 H represents a 366 1~366- pyridylcombination of 710 substituents corresponding to each row of Table BTable 367- 5-Chloro-2- A-34 H represents a 367 1~367- pyridylcombination of 710 substituents corresponding to each row of Table BTable 368- 6-Chloro-2- A-35 H represents a 368 1~368- pyridylcombination of 710 substituents corresponding to each row of Table BTable 369- 2-Chloro-3- A-36 H represents a 369 1~369- pyridylcombination of 710 substituents corresponding to each row of Table BTable 370- 5-Chloro-3- A-37 H represents a 370 1~370- pyridylcombination of 710 substituents corresponding to each row of Table BTable 371- 6-Chloro-3- A-38 H represents a 371 1~371- pyridylcombination of 710 substituents corresponding to each row of Table BTable 372- 4-Chloro-3- A-39 H represents a 372 1~372- pyridylcombination of 710 substituents corresponding to each row of Table BTable 373- 2-Chloro-4- A-40 H represents a 373 1~373- pyridylcombination of 710 substituents corresponding to each row of Table BTable 374- 3-Chloro-4- A-2 H represents a 374 1~374- pyridyl combinationof 710 substituents corresponding to each row of Table B Table 375-3-bromo-2- A-3 H represents a 375 1~375- pyridyl combination of 710substituents corresponding to each row of Table B Table 376- 4-bromo-2-A-4 H represents a 376 1~376- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 377- 5-bromo-2- A-5 Hrepresents a 377 1~377- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 378- 6-bromo-2- A-6 Hrepresents a 378 1~378- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 379- 2-bromo-3- A-7 Hrepresents a 379 1~379- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 380- 5-bromo-3- A-8 Hrepresents a 380 1~380- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 381- 6-bromo-3- A-9 Hrepresents a 381 1~381- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 382- 4-bromo-3- A-10 Hrepresents a 382 1~382- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 383- 2-bromo-4- A-11 Hrepresents a 383 1~383- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 384- 3-bromo-4- A-12 Hrepresents a 384 1~384- pyridyl combination of 710 substituentscorresponding to each row of Table B

TABLE 13 Table A Compound No Ar A Y R Table 385- 3-Fluoro-2- A-17 Hrepresents a 385 1~385- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 386- 4-Fluoro-2- A-18 Hrepresents a 386 1~386- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 387- 5-Fluoro-2- A-19 Hrepresents a 387 1~387- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 388- 6-Fluoro-2- A-20 Hrepresents a 388 1~388- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 389- 2-Fluoro-3- A-21 Hrepresents a 389 1~389- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 390- 5-Fluoro-3- A-22 Hrepresents a 390 1~390- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 391- 6-Fluoro-3- A-23 Hrepresents a 391 1~391- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 392- 4-Fluoro-3- A-24 Hrepresents a 392 1~392- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 393- 2-Fluoro-4- A-25 Hrepresents a 393 1~393- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 394- 3-Fluoro-4- A-26 Hrepresents a 394 1~394- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 395- 6-Fluoro-3- A-27 Hrepresents a 395 1~395- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 396- 3-iodo-2- A-28 Hrepresents a 396 1~396- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 397- 4-iodo-2- A-29 Hrepresents a 397 1~397- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 398- 5-iodo-2- A-30 Hrepresents a 398 1~398- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 399- 6-iodo- A-31 Hrepresents a 399 1~399- 2~pyridyl combination of 710 substituentscorresponding to each row of Table B Table 400- 2-iodo-3- A-32 Hrepresents a 400 1~400- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 401- 5-iodo-3- A-33 Hrepresents a 401 1~401- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 402- 6-iodo-3- A-34 Hrepresents a 402 1~402- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 403- 4-iodo-3- A-35 Hrepresents a 403 1~403- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 404- 2-iodo-4- A-36 Hrepresents a 404 1~404- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 405- 3-iodo-4- A-37 Hrepresents a 405 1~405- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 406- 6-iodo-3- A-38 Hrepresents a 406 1~406- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 407- 6-iodo-3- A-39 Hrepresents a 407 1~407- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 408- 2- A-40 H represents a408 1~408- tetrahydrofuranyl combination of 710 substituentscorresponding to each row of Table B Table 409- 3- A-2 H represents a409 1~409- tetrahydrofuranyl combination of 710 substituentscorresponding to each row of Table B Table 410- 5-Chloro-2- A-3 Hrepresents a 410 1~410- thiazolyl combination of 710 substituentscorresponding to each row of Table B Table 411- 6-Fluoro-3- A-4 Hrepresents a 411 1~411- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 412- 6-Bromo-3- A-5 Hrepresents a 412 1~412- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 413- 6-Chloro-5- A-6 Hrepresents a 413 1~413- Fluoro-3- combination of 710 pyridylsubstituents corresponding to each row of Table B Table 414- 3,5- A-7 Hrepresents a 414 1~414- Dimethylphenyl combination of 710 substituentscorresponding to each row of Table B Table 415- 2,3- A-8 H represents a415 1~415- Dimethylphenyl combination of 710 substituents correspondingto each row of Table B Table 416- 2,4- A-9 H represents a 416 1~416-Dimethyophenyl combination of 710 substituents corresponding to each rowof Table B

TABLE 14 Table A Compound No Ar A Y R Table 417- Phenyl A-10 Hrepresents a 417 1~417- combination of 710 substituents corresponding toeach row of Table B Table 418- cyclopentyl A-11 H represents a 4181~418- combination of 710 substituents corresponding to each row ofTable B Table 419- cyclohexyl A-12 H represents a 419 1~419- combinationof 710 substituents corresponding to each row of Table B Table 420- 3-A-17 H represents a 420 1~420- methylcyclohexyl combination of 710substituents corresponding to each row of Table B Table 421- cyclobutylA-18 H represents a 421 1~421- combination of 710 substituentscorresponding to each row of Table B Table 422- 2-oxetanyl A-19 Hrepresents a 422 1~422- combination of 710 substituents corresponding toeach row of Table B Table 423- 3-oxetanyl A-20 H represents a 423 1~423-combination of 710 substituents corresponding to each row of Table BTable 424- 2-thietanyl A-21 H represents a 424 1~424- combination of 710substituents corresponding to each row of Table B Table 425- 3-thietanylA-22 H represents a 425 1~425- combination of 710 substituentscorresponding to each row of Table B Table 426- 2-azetidinyl A-23 Hrepresents a 426 1~426- combination of 710 substituents corresponding toeach row of Table B Table 427- 3-azetidinyl A-24 H represents a 4271~427- combination of 710 substituents corresponding to each row ofTable B Table 428- 6-iodo-3- A-25 H represents a 428 1~428- pyridylcombination of 710 substituents corresponding to each row of Table BTable 429- 6-iodo-3- A-26 H represents a 429 1~429- pyridyl combinationof 710 substituents corresponding to each row of Table B Table 430- 2-A-27 H represents a 430 1~430- tetrahydrofuranyl combination of 710substituents corresponding to each row of Table B Table 431- 2-Chloro-3-A-28 H represents a 431 1~431- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 432- 5-Chloro-3- A-29 Hrepresents a 432 1~432- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 433- 6-Chloro-3- A-30 Hrepresents a 433 1~433- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 434- 4-Chloro-3- A-31 Hrepresents a 434 1~434- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 435- 2-Chloro-4- A-32 Hrepresents a 435 1~435- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 436- 3-Chloro-4- A-33 Hrepresents a 436 1~436- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 437- 3-bromo-2- A-34 Hrepresents a 437 1~437- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 438- 4-bromo-2- A-35 Hrepresents a 438 1~438- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 439- 2-FIuoro-4- A-36 Hrepresents a 439 1~439- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 440- 3-Fluoro-4- A-37 Hrepresents a 440 1~440- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 441- 6-Fluoro-3- A-38 Hrepresents a 441 1~441- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 442- 3-iodo-2- A-39 Hrepresents a 442 1~442- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 443- 6-Fluoro-3- A-40 Hrepresents a 443 1~443- pyridyl combination of 710 substituentscorresponding to each row of Table B Table 444- 2-Chloro-5- A-38 Hrepresents a 444 1~444- thiazolyl combination of 710 substituentscorresponding to each row of Table B

TABLE 15 Table A Compound No. Ar A Y R Table 445- 6-Chloro-3- A-1 3-represents a 445 1~445- pyridyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 446- 2-Chloro-5- A-1 3-represents a 446 1~446- thiazolyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 447- 6-Fluoro-3- A-1 3-represents a 447 1~447- pyridyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 448- 6-Bromo-3- A-1 3-represents a 448 1~448- pyridyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 449- 6-Chloro-5- A-1 3-represents a 449 1~449- fluoro-3- CH3 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 450- 2-Chloro-5-A-1 3- represents a 450 1~450- pyrimidinyl CH3 combination of 710substituents corresponding to each row of Table B Table 451- 5- A-1 3-represents a 451 1~451- Chloro- CH3 combination of 710 pyrazin-2-ylsubstituents corresponding to each row of Table B Table 452- 6- A-1 3-represents a 452 1~452- Chloro- CH3 combination of 710 pyridazin-3-ylsubstituents corresponding to each row of Table B Table 453- 2-Chloro-5-A-1 3- represents a 453 1~453- oxazolyl CH3 combination of 710substituents corresponding to each row of Table B Table 454- 6- A-1 3-represents a 454 1~454- trifluoromethyl-3- CH3 combination of 710pyridyl substituents corresponding to each row of Table B Table 455- 3-A-1 3- represents a 455 1~455- tetrahydro- CH3 combination of 710furanyl substituents corresponding to each row of Table B Table 456-6-Chloro-3- A-1 4- represents a 456 1~456- pyridyl CH3 combination of710 substituents corresponding to each row of Table B Table 457-2-Chloro-5- A-1 4- represents a 457 1~457- thiazolyl CH3 combination of710 substituents corresponding to each row of Table B Table 458-6-Fluoro-3- A-1 4- represents a 458 1~458- pyridyl CH3 combination of710 substituents corresponding to each row of Table B Table 459-6-Bromo-3- A-1 4- represents a 459 1~459- pyridyl CH3 combination of 710substituents corresponding to each row of Table B Table 460- 6-Chloro-5-A-1 4- represents a 460 1~460- Fluoro-3- CH3 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 461- 2-Chloro-5-A-1 4- represents a 461 1~461- pyrimidinyl CH3 combination of 710substituents corresponding to each row of Table B Table 462- 5- A-1 4-represents a 462 1~462- Chloro- CH3 combination of 710 pyrazin-2-ylsubstituents corresponding to each row of Table B Table 463- 6- A-1 4-represents a 463 1~463- Chloro- CH3 combination of 710 pyridazin-3-ylsubstituents corresponding to each row of Table B Table 464- 2-Chloro-5-A-1 4- represents a 464 1~464- oxazolyl CH3 combination of 710substituents corresponding to each row of Table B Table 465- 6- A-1 4-represents a 465 1~465- trifluoromethyl-3- CH3 combination of 710pyridyl substituents corresponding to each row of Table B Table 466- 3-A-1 4- represents a 466 1~466- tetrahydro- CH3 combination of 710furanyl substituents corresponding to each row of Table B Table 467-6-Chloro-3- A-1 5- represents a 467 1~467- pyridyl CH3 combination of710 substituents corresponding to each row of Table B Table 468-2-Chloro-5- A-1 5- represents a 468 1~468- thiazolyl CH3 combination of710 substituents corresponding to each row of Table B Table 469-6-Fluoro-3- A-1 5- represents a 469 1~469- pyridyl CH3 combination of710 substituents corresponding to each row of Table B Table 470-6-Bromo-3- A-1 5- represents a 470 1~470- pyridyl CH3 combination of 710substituents corresponding to each row of Table B Table 471- 6-Chloro-5-A-1 5- represents a 471 1~471- fluoro-3- CH3 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 472- 2-Chloro-5-A-1 5- represents a 472 1~472- pyrimidinyl CH3 combination of 710substituents corresponding to each row of Table B Table 473- 5- A-1 5-represents a 473 1~473- Chloro- CH3 combination of 710 pyrazin-2-ylsubstituents corresponding to each row of Table B Table 474- 6- A-1 5-represents a 474 1~474- Chloro- CH3 combination of 710 pyridazin-3-ylsubstituents corresponding to each row of Table B Table 475- 2-Chloro-5-A-1 5- represents a 475 1~475- oxazolyl CH3 combination of 710substituents corresponding to each row of Table B Table 476- 6- A-1 5-represents a 476 1~476- trifluoro- CH3 combination of 710 methyl-3-substituents pyridyl corresponding to each row of Table B

TABLE 16 Table A Compound No. Ar A Y R Table 477- 3- A-1 5- represents a477 1~477- tetrahydrofuranyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 478- 6-Chloro-3- A-1 6-represents a 478 1~478- pyridyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 479- 2-Chloro-5- A-1 6-represents a 479 1~479- thiazolyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 480- 6-Fluoro-3- A-1 6-represents a 480 1~480- pyridyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 481- 6-Bromo-3- A-1 6-represents a 481 1~481- pyridyl CH3 combination of 710 substituentscorresponding to each row of Table B Table 482- 6-Chloro-5- A-1 6-represents a 482 1~482- fluoro-3- CH3 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 483- 2-Chloro-5-A-1 6- represents a 483 1~483- pyrimidinyl CH3 combination of 710substituents corresponding to each row of Table B Table 484- 5- A-1 6 -represents a 484 1~484- Chloropyrazin- CH3 combination of 710 2-ylsubstituents corresponding to each row of Table B Table 485- 6- A-1 6 -represents a 485 1~485- Chloropyridazin- CH3 combination of 710 3-ylsubstituents corresponding to each row of Table B Table 486- 2-Chloro-5-A-1 6 - represents a 486 1~486- oxazolyl CH3 combination of 710substituents corresponding to each row of Table B Table 487- 6- A-1 6 -represents a 487 1~487- trifluoromethyl- CH3 combination of 7103-pyridyl substituents corresponding to each row of Table B Table 488-3- A-1 6- represents a 488 1~488- tetrahydrofuranyl CH3 combination of710 substituents corresponding to each row of Table B Table 489-6-Chloro-3- A-1 3- represents a 489 1~489- pyridyl NO2 combination of710 substituents corresponding to each row of Table B Table 490-2-Chloro-5- A-1 3- represents a 490 1~490- thiazolyl NO2 combination of710 substituents corresponding to each row of Table B Table 491-6-Fluoro-3- A-1 3- represents a 491 1~491- pyridyl NO2 combination of710 substituents corresponding to each row of Table B Table 492-6-Bromo-3- A-1 3- represents a 492 1~492- pyridyl NO2 combination of 710substituents corresponding to each row of Table B Table 493- 6-Chloro-5-A-1 3- represents a 493 1~493- Fluoro-3- NO2 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 494- 2-Chloro-5-A-1 3- represents a 494 1~494- pyrimidinyl NO2 combination of 710substituents corresponding to each row of Table B Table 495- 5- A-1 3-represents a 495 1~495- Chloropyrazin- NO2 combination of 710 2-ylsubstituents corresponding to each row of Table B Table 496- 6- A-1 3-represents a 496 1~496- Chloropyridazin- NO2 combination of 710 3-ylsubstituents corresponding to each row of Table B Table 497- 2-Chloro-5-A-1 3- represents a 497 1~497- oxazolyl NO2 combination of 710substituents corresponding to each row of Table B Table 498- 6- A-1 3-represents a 498 1~498- trifluoromethyl- NO2 combination of 7103-pyridyl substituents corresponding to each row of Table B Table 499-3- A-1 3- represents a 499 1~499- tetrahydrofuranyl NO2 combination of710 substituents corresponding to each row of Table B Table 500-6-Chloro-3- A-1 4- represents a 500 1~500- pyridyl NO2 combination of710 substituents corresponding to each row of Table B Table 501-2-Chloro-5- A-1 4- represents a 501 1~501- thiazolyl NO2 combination of710 substituents corresponding to each row of Table B Table 502-6-Fluoro-3- A-1 4- represents a 502 1~502- pyridyl NO2 combination of710 substituents corresponding to each row of Table B Table 503-6-Bromo-3- A-1 4- represents a 503 1~503- pyridyl NO2 combination of 710substituents corresponding to each row of Table B Table 504- 6-Chloro-5-A-1 4- represents a 504 1~504- fluoro-3- NO2 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 505- 2-Chloro-5-A-1 4- represents a 505 1~505- pyrimidinyl NO2 combination of 710substituents corresponding to each row of Table B Table 506- 5- A-1 4-represents a 506 1~506- Chloropyrazin- NO2 combination of 710 2-ylsubstituents corresponding to each row of Table B Table 507- 6- A-1 4-represents a 507 1~507- Chloropyridazin- NO2 combination of 710 3-ylsubstituents corresponding to each row of Table B Table 508- 2-Chloro-5-A-1 4- represents a 508 1~508- oxazolyl NO2 combination of 710substituents corresponding to each row of Table B

TABLE 17 Table A Compound No. Ar A Y R Table 509- 6- A-1 4- represents a509 1~509- trifluoromethyl- NO2 combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 510- 3- A-1 4-represents a 510 1~510- tetrahydrofuranyl NO2 combination of 710substituents corresponding to each row of Table B Table 511- 6-Chloro-3-A-1 5- represents a 511 1~511- pyridyl NO2 combination of 710substituents corresponding to each row of Table B Table 512- 2-Chloro-5-A-1 5- represents a 512 1~512- thiazolyl NO2 combination of 710substituents corresponding to each row of Table B Table 513- 6-Fluoro-3-A-1 5- represents a 513 1~513- pyridyl NO2 combination of 710substituents corresponding to each row of Table B Table 514- 6-Bromo-3-A-1 5- represents a 514 1~514- pyridyl NO2 combination of 710substituents corresponding to each row of Table B Table 515- 6-Chloro-5-A-1 5- represents a 515 1~515- fluoro-3- NO2 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 516- 2-Chloro-5-A-1 5- represents a 516 1~516- pyrimidinyl NO2 combination of 710substituents corresponding to each row of Table B Table 517- 5- A-1 5-represents a 517 1~517- Chloropyrazin- NO2 combination of 710 2-ylsubstituents corresponding to each row of Table B Table 518- 6- A-1 5-represents a 518 1~518- Chloropyridazin- NO2 combination of 710 3-ylsubstituents corresponding to each row of Table B Table 519- 2-Chloro-5-A-1 5- represents a 519 1~519- oxazolyl NO2 combination of 710substituents corresponding to each row of Table B Table 520- 6- A-1 5-represents a 520 1~520- trifluoromethyl- NO2 combination of 7103-pyridyl substituents corresponding to each row of Table B Table 521-3- A-1 5- represents a 521 1~521- tetrahydrofuranyl NO2 combination of710 substituents corresponding to each row of Table B Table 522-6-Chloro-3- A-1 6- represents a 522 1~522- pyridyl NO2 combination of710 substituents corresponding to each row of Table B Table 523-2-Chloro-5- A-1 6- represents a 523 1~523- thiazolyl NO2 combination of710 substituents corresponding to each row of Table B Table 524-6-Fluoro-3- A-1 6- represents a 524 1~524- pyridyl NO2 combination of710 substituents corresponding to each row of Table B Table 525-6-Bromo-3- A-1 6- represents a 525 1~525- pyridyl NO2 combination of 710substituents corresponding to each row of Table B Table 526- 6-Chloro-5-A-1 6- represents a 526 1~526- Fluoro-3- NO2 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 527- 2-Chloro-5-A-1 6- represents a 527 1~527- pyrimidinyl NO2 combination of 710substituents corresponding to each row of Table B Table 528- 5- A-1 6-represents a 528 1~528- Chloropyrazin- NO2 combination of 710 2-ylsubstituents corresponding to each row of Table B Table 529- 6- A-1 6-represents a 529 1~529- Chloropyridazin- NO2 combination of 710 3-ylsubstituents corresponding to each row of Table B Table 530- 2-Chloro-5-A-1 6- represents a 530 1~530- oxazolyl NO2 combination of 710substituents corresponding to each row of Table B Table 531- 6- A-1 6-represents a 531 1~531- trifluoromethyl- NO2 combination of 7103-pyridyl substituents corresponding to each row of Table B Table 532-3- A-1 6- represents a 532 1~532- tetrahydrofuranyl NO2 combination of710 substituents corresponding to each row of Table B Table 533-6-Chloro-3- A-1 3- represents a 533 1~533- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 534-2-Chloro-5- A-1 3- represents a 534 1~534- thiazolyl OCH3 combination of710 substituents corresponding to each row of Table B Table 535-6-Fluoro-3- A-1 3- represents a 535 1~535- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 536-6-Bromo-3- A-1 3- represents a 536 1~536- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 537-6-Chloro-5- A-1 3- represents a 537 1~537- fluoro-3- OCH3 combination of710 pyridyl substituents corresponding to each row of Table B Table 538-2-Chloro-5- A-1 3- represents a 538 1~538- pyrimidinyl OCH3 combinationof 710 substituents corresponding to each row of Table B Table 539- 5-A-1 3- represents a 539 1~539- Chloropyrazin- OCH3 combination of 7102-yl substituents corresponding to each row of Table B Table 540- 6- A-13- represents a 540 1~540- Chloropyridazin- OCH3 combination of 710 3-ylsubstituents corresponding to each row of Table B

TABLE 18 Table A Compound No. Ar A Y R Table 541- 2-Chloro-5- A-1 3-represents a 541 1~541- oxazolyl OCH3 combination of 710 substituentscorresponding to each row of Table B Table 542- 6- A-1 3- represents a542 1~542- trifluoromethyl- OCH3 combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 543- 3- A-1 3-represents a 543 1~543- tetrahydrofuranyl OCH3 combination of 710substituents corresponding to each row of Table B Table 544- 6-Chloro-3-A-1 4- represents a 544 1~544- pyridyl OCH3 combination of 710substituents corresponding to each row of Table B Table 545- 2-Chloro-5-A-1 4- represents a 545 1~545- thiazolyl OCH3 combination of 710substituents corresponding to each row of Table B Table 546- 6-Fluoro-3-A-1 4- represents a 546 1~546- pyridyl OCH3 combination of 710substituents corresponding to each row of Table B Table 547- 6-Bromo-3-A-1 4- represents a 547 1~547- pyridyl OCH3 combination of 710substituents corresponding to each row of Table B Table 548- 6-Chloro-5-A-1 4- represents a 548 1~548- Fluoro-3- OCH3 combination of 710 pyridylsubstituents corresponding to each row of Table B Table 549- 2-Chloro-5-A-1 4- represents a 549 1~549- pyrimidinyl OCH3 combination of 710substituents corresponding to each row of Table B Table 550- 5- A-1 4-represents a 550 1~550- Chloropyrazin- OCH3 combination of 710 2-ylsubstituents corresponding to each row of Table B Table 551- 6- A-1 4-represents a 551 1~551- Chloropyridazin- OCH3 combination of 710 3-ylsubstituents corresponding to each row of Table B Table 552- 2-Chloro-5-A-1 4- represents a 552 1~552- oxazolyl OCH3 combination of 710substituents corresponding to each row of Table B Table 553- 6- A-1 4-represents a 553 1~553- trifluoromethyl- OCH3 combination of 7103-pyridyl substituents corresponding to each row of Table B Table 554-3- A-1 4- represents a 554 1~554- tetrahydrofuranyl OCH3 combination of710 substituents corresponding to each row of Table B Table 555-6-Chloro-3- A-1 5- represents a 555 1~555- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 556-2-Chloro-5- A-1 5- represents a 556 1~556- thiazolyl OCH3 combination of710 substituents corresponding to each row of Table B Table 557-6-Fluoro-3- A-1 5- represents a 557 1~557- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 558-6-Bromo-3- A-1 5- represents a 558 1~558- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 559-6-Chloro-5- A-1 5- represents a 559 1~559- fluoro-3- OCH3 combination of710 pyridyl substituents corresponding to each row of Table B Table 560-2-Chloro-5- A-1 5- represents a 560 1~560- pyrimidinyl OCH3 combinationof 710 substituents corresponding to each row of Table B Table 561- 5-A-1 5- represents a 561 1~561- Chloropyrazin- OCH3 combination of 7102-yl substituents corresponding to each row of Table B Table 562- 6- A-15- represents a 562 1~562- Chloropyridazin- OCH3 combination of 710 3-ylsubstituents corresponding to each row of Table B Table 563- 2-Chloro-5-A-1 5- represents a 563 1~563- oxazolyl OCH3 combination of 710substituents corresponding to each row of Table B Table 564- 6- A-1 5-represents a 564 1~564- trifluoromethyl- OCH3 combination of 7103-pyridyl substituents corresponding to each row of Table B Table 565-3- A-1 5- represents a 565 1~565- tetrahydrofuranyl OCH3 combination of710 substituents corresponding to each row of Table B Table 566-6-Chloro-3- A-1 6 - represents a 566 1~566- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 567-2-Chloro-5- A-1 6 - represents a 567 1~567- thiazolyl OCH3 combinationof 710 substituents corresponding to each row of Table B Table 568-6-Fluoro-3- A-1 6 - represents a 568 1~568- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 569-6-Bromo-3- A-1 6 - represents a 569 1~569- pyridyl OCH3 combination of710 substituents corresponding to each row of Table B Table 570-6-Chloro-5- A-1 6 - represents a 570 1~570- Fluoro-3- OCH3 combinationof 710 pyridyl substituents corresponding to each row of Table B Table571- 2-Chloro-5- A-1 6 - represents a 571 1~571- pyrimidinyl OCH3combination of 710 substituents corresponding to each row of Table BTable 572- 5- A-1 6- represents a 572 1~572- Chloropyrazin- OCH3combination of 710 2-yl substituents corresponding to each row of TableB

TABLE 19 Table A Compound No. Ar A Y R Table 573- 6- A-1 6- represents a573 1~573- Chloropyridazin- OCH3 combination of 710 3-yl substituentscorresponding to each row of Table B Table 574- 2-Chloro-5- A-1 6-represents a 574 1~574- oxazolyl OCH3 combination of 710 substituentscorresponding to each row of Table B Table 575- 6- A-1 6- represents a575 1~575- trifluoromethyl- OCH3 combination of 710 3-pyridylsubstituents corresponding to each row of Table B Table 576- 3- A-1 6-represents a 576 1~576- tetrahydrofuranyl OCH3 combination of 710substituents corresponding to each row of Table B Table 577- 2,6- A-1 Hrepresents a 577 1~577- dichloro-3- combination of 710 pyridylsubstituents corresponding to each row of Table B Table 578- 3-pyridylA-1 H represents a 578 1~578- combination of 710 substituentscorresponding to each row of Table B Table 579- 4-pyridyl A-1 Hrepresents a 579 1~579- combination of 710 substituents corresponding toeach row of Table B Table 580- 6-chloro-3- A-1 H represents a 580 1~580-pyridyl-N- combination of 710 oxide substituents corresponding to eachrow of Table B

TABLE B Table 20 R

    R1 1 H 2 CF3 3 CHF2 4 CF2Cl 5 CF2CF3 6 CH2Cl 7 CHCl2 8 CCl3 9 CHClBr10 2,2- difluorocyclopropyl 11 2,3,3- trifluoroacryl 12 CH2CHF2 13CH2CF3 14 CH═CH2 15 CH2C≡CH 16 CH2CH2C≡CH

    R2 17 CH2CF3 18 CH(Me)CF3 19 CH(CF3)2

    R3 20 CF3 21 CHF2 22 CF2Cl 23 CF2CF3 24 CH2Cl 25 CHCl2 26 CCl3 27CHClBr 28 CHBr2 29 2,3,3- trifluoroacryl 30 CH2CHF2 31 CH2CF3 32 CH═CH233 CH2C≡CH 34 CH2CF3 35 CH2CH2Ph 36 Me 37 Et 38 n-Pr 39 i-Pr 40cyclopropyl Table 21 R

R4 R5 41 H CF3 42 Me CF3 43 Et CF3 44 n-Pr CF3 45 i-Pr CF3 46 t-Bu CF347 n-Bu CF3 48 n-Pentyl CF3 49 n-Hexyl CF3 50 cyclopropyl CF3 51cyclobutyl CF3 52 cyclopentyl CF3 53 cyclohexyl CF3 54 CH═CH2 CF3 55CH2CH═CH2 CF3 56 CH2C≡CH CF3 57 CH2CH2CΞCH CF3 58 CH2CHF2 CF3 59 CH2CCF3CF3 60 CH2CH2Cl CF3 61 CH2CHCl2 CF3 62 2-fluoro-2- CF3 chloroethyl 63CH2CCl3 CF3 64 CH2CN CF3 65 CH2CH2CN CF3 66 CH2CH(CN)CH2CN CF3 67CH2CH2OH CF3 68 CH2CH2HC2OH CF3 69 CH2CH(OH)CH2OH CF3 70 CH2CH2NO2 CF371 Phenyl CF3 72 CH2-Phenyl CF3 73 CH(Me)-Phenyl CF3 74 C(Me2)-PhenylCF3 75 C(cyclopropyl)- CF3 Phenyl 76 CH2CH2-Phenyl CF3 77 CH2-(2- CF3Methylphenyl) 78 CH2-(3- CF3 Methylphenyl) 79 CH2-(4- CF3 Methylphenyl)80 CH2-(2- CF3 Methoxylphenyl) 81 CH2-(3- CF3 Methoxylphenyl) 82 CH2-(4-CF3 Methoxylphenyl) 83 CH2-(2- CF3 fluorolphenyl) 84 CH2-(3- CF3fluorolphenyl) 85 CH2-(4- CF3 fluorolphenyl) 86 CH2-(2- Chlorophenyl) 87CH2-(3- CF3 Chlorophenyl) 88 CH2-(4- CF3 Chlorophenyl) 89 CH2-(2- CF3Bromophenyl) 90 CH2-(3- CF3 Bromophenyl) 91 CH2-(4- CF3 Bromophenyl) 92CH2-(2- CF3 iodophenyl) 93 CH2-(3- CF3 iodophenyl) Table 22 94 CH2-(4-CF3 iodophenyl) 95 CH2-(1- CF3 naphthalenyl) 96 CH2-(2- CF3naphthalenyl) 97 naphthalen-1- CF3 ylmethyl 98 naphthalen-2- CF3ylmethyl 99 quinolin-2- CF3 ylmethyl 100 quinolin-7- CF3 ylmethyl 101isoquinolin- CF3 7-ylmethyl 102 isoquinolin- CF3 6-ylmethyl 103quinolin-6- CF3 ylmethyl 104 quinolin-3- CF3 ylmethyl 105 isoquinolin-CF3 3-ylmethyl 106 isoquinolin- CF3 1-ylmethyl 107 isoquinolin- CF34-ylmethyl 108 quinolin-4- CF3 ylmethyl 109 quinolin-5- CF3 ylmethyl 110isoquinolin- CF3 5-ylmethyl 111 isoquinolin- CF3 8-ylmethyl 112quinolin-8- CF3 ylmethyl 113 CH2O-Phenyl CF3 114 CH2CH2O-Phenyl CF3 1152-pyridyl CF3 116 3-pyridyl CF3 117 4-pyridyl CF3 118 CH2-(2- CF3pyridyl) 119 CH2-(3- CF3 pyridyl) 120 CH2-(4-Chloro- CF3 3-pyridyl) 121CH2-(4- CF3 pyridyl) 122 CH2-(2- CF3 thienyl) 123 CH2-(3- CF3 thienyl)124 CH2-(2- CF3 furanyl) 125 CH2-(3- CF3 furanyl) 126 CH2-(2- CF3tetrahydrofuranyl) 127 CH2-(3- CF3 tetrahydrofuranyl) 128(1H-imidazol-2- CF3 yl)methyl 129 (1H-imidazol-1- CF3 yl)methyl 130(1H-imidazol-4- CF3 yl)methyl 131 CH2-(2- CF3 thiazolyl) 132 CH2-(3- CF3thiazolyl) 133 CH2-(2-pyrrolyl) CF3 134 CH2-(3-pyrrolyl) CF3 135 CH2-(5-CF3 methylpyrazol-1-yl) 136 CH2-(1- CF3 pyrazolyl) 137 CH2-(2- CF3pyrazolyl) 138 CH2-(3- CF3 pyrazolyl) 139 CH2-(4- CF3 pyrazolyl) 140CH2-(5- CF3 pyrazolyl) 141 CH2-(2- CF3 oxazolyl) 142 CH2-(3- CF3oxazolyl) 143 CH2-(3- CF3 isoxazolyl) 144 CH2-(4- CF3 isoxazolyl) 145CH2-(5- CF3 isoxazolyl) 146 CH2CH2OCH3 CF3 147 CH2CH2OCH2CH3 CF3 Table23 148 CH2CH2CH2OCH3 CF3 149 CH2CH2CH2OCH2CH3 CF3 150 CH2CH2SCH3 CF3 151CH2CH2SCH2CH3 CF3 152 CH2CH2CH2SCH3 CF3 153 CH2CH2CH2SCH2CH3 CF3 154 MeCHF2 155 Et CHF2 156 n-Pr CHF2 157 i-Pr CHF2 158 t-Bu CHF2 159 n-Bu CHF2160 n-Pentyl CHF2 161 n-Hexyl CHF2 162 cyclopropyl CHF2 163 cyclobutylCHF2 164 cyclopentyl CHF2 165 cyclohexyl CHF2 166 CH═CH2 CHF2 167CH2CH═CH2 CHF2 168 CH2C≡CH CHF2 169 CH2CH2C≡CH CHF2 170 CH2CHF2 CHF2 171CH2CCF3 CHF2 172 CH2CH2Cl CHF2 173 CH2CHCl2 CHF2 174 2-fluoro-2- CHF2chloroethyl 175 CH2CCl3 CHF2 176 CH2CH2CN CHF2 177 CH2CH2CH2CN CHF2 178CH2CH(CN)CH2CN CHF2 179 CH2CH2OH CHF2 180 CH2CH2CH2OH CHF2 181CH2CH(OH)CH2OH CHF2 182 CH2CH2NO2 CHF2 183 Phenyl CHF2 184 CH2-PhenylCHF2 185 CH(Me)-Phenyl CHF2 186 C(Me2)-Phenyl CHF2 187 C(cyclopropyl)-CHF2 Phenyl 188 CH2CH2-Phenyl CHF2 189 CH2-(2- CHF2 Methylphenyl) 190CH2-(3- CHF2 Methylphenyl) 191 CH2-(4- CHF2 Methylphenyl) 192 CH2-(2-CHF2 Methoxylphenyl) 193 CH2-(3- CHF2 Methoxylphenyl) 194 CH2-(4- CHF2Methoxylphenyl) 195 CH2-(2- CHF2 fluorolphenyl) 196 CH2-(3- CHF2fluorolphenyl) 197 CH2-(4- CHF2 fluorolphenyl) 198 CH2-(2- CHF2Chlorophenyl) 199 CH2-(3- CHF2 Chlorophenyl) 200 CH2-(4- CHF2Chlorophenyl) 201 CH2-(2- CHF2 Bromophenyl) Table 24 202 CH2-(3- CHF2Bromophenyl) 203 CH2-(4- CHF2 Bromophenyl) 204 CH2-(2- CHF2 iodophenyl)205 CH2-(3- CHF2 iodophenyl) 206 CH2-(4- CHF2 iodophenyl) 207 CH2-(1-CHF2 naphthalenyl) 208 CH2-(2- CHF2 naphthalenyl) 209 naphthalen-1- CHF2ylmethyl 210 naphthalen-2- CHF2 ylmethyl 211 quinolin-2- CHF2 ylmethyl212 quinolin-7- CHF2 ylmethyl 213 isoquinolin- CHF2 7-ylmethyl 214isoquinolin- CHF2 6-ylmethyl 215 quinolin-6- CHF2 ylmethyl 216quinolin-3- CHF2 ylmethyl 217 isoquinolin- CHF2 3-ylmethyl 218isoquinolin- CHF2 1-ylmethyl 219 isoquinolin- CHF2 4-ylmethyl 220quinolin-4- CHF2 ylmethyl 221 quinolin-5- CHF2 ylmethyl 222 isoquinolin-CHF2 5-ylmethyl 223 isoquinolin- CHF2 8-ylmethyl 224 quinolin-8- CHF2ylmethyl 225 CH2O-Phenyl CHF2 226 CH2CH2O-Phenyl CHF2 227 2-pyridyl CHF2228 3-pyridyl CHF2 229 4-pyridyl CHF2 230 CH2-(2- CHF2 pyridyl) 231CH2-(3- CHF2 pyridyl) 232 CH2-(4- CHF2 Chloro-3- pyridyl) 233 CH2-(4-CHF2 pyridyl) 234 CH2-(2- CHF2 thienyl) 235 CH2-(3-thienyl) CHF2 236CH2-(2-furanyl) CHF2 237 CH2-(3-furanyl) CHF2 238 CH2-(2- CHF2tetrahydrofuranyl) 239 CH2-(3- CHF2 tetrahydrofuranyl) 240(1H-imidazol-2- CHF2 yl)methyl 241 (1H-imidazol-1- CHF2 yl)methyl 242(1H-imidazol-4- CHF2 yl)methyl 243 CH2-(2- CHF2 thiazolyl) 244 CH2-(3-CHF2 thiazolyl) 245 CH2-(2-pyrrolyl) CHF2 246 CH2-(3- CHF2 pyrrolyl) 247CH2-(5- CHF2 methylpyrazol-1-yl) 248 CH2-(1- CHF2 pyrazolyl) 249 CH2-(2-CHF2 pyrazolyl) 250 CH2-(3- CHF2 pyrazolyl) 251 CH2-(4- CHF2 pyrazolyl)252 CH2-(5- CHF2 pyrazolyl) 253 CH2-(2- CHF2 oxazolyl) 254 CH2-(3- CHF2oxazolyl 255 CH2-(3- CHF2 isoxazolyl) Table 25 256 CH2-(4- CHF2isoxazolyl) 257 CH2-(5- CHF2 isoxazolyl) 258 CH2CH2OCH3 CHF2 259CH2CH2OCH2CH3 CHF2 260 CH2CH2CH2OCH3 CHF2 261 CH2CH2CH2OCH2CH3 CHF2 262CH2CH2SCH3 CHF2 263 CH2CH2SCH2CH3 CHF2 264 CH2CH2CH2SCH3 CHF2 265CH2CH2CH2SCH2CH3 CHF2 266 Me CF2Cl 267 Et CF2Cl 268 n-Pr CF2Cl 269 i-PrCF2Cl 270 t-Bu CF2Cl 271 n-Bu CF2Cl 272 n-Pentyl CF2Cl 273 n-Hexyl CF2Cl274 cyclopropyl CF2Cl 275 cyclobutyl CF2Cl 276 cyclopentyl CF2Cl 277cyclohexyl CF2Cl 278 CH═CH2 CF2Cl 279 CH2CH═CH2 CF2Cl 280 CH2C≡CH CF2Cl281 CH2CH2C≡CH CF2Cl 282 CH2CHF2 CF2Cl 283 CH2CCF3 CF2Cl 284 CH2CH2ClCF2Cl 285 CH2CHCl2 CF2Cl 286 2-fluoro-2- CF2Cl chloroethyl 287 CH2CCl3CF2Cl 288 CH2CH2CN CF2Cl 289 CH2CH2CH2CN CF2Cl 290 CH2CH(CN)CH2CN CF2Cl291 CH2CH2OH CF2Cl 292 CH2CH2CH2OH CF2Cl 293 CH2CH(OH)CH2OH CF2Cl 294CH2CH2NO2 CF2Cl 295 Phenyl CF2Cl 296 CH2-Phenyl CF2Cl 297 CH(Me)-PhenylCF2Cl 298 C(Me2)-Phenyl CF2Cl 299 C(cyclopropyl)- CF2Cl Phenyl 300CH2CH2-Phenyl CF2Cl 301 CH2-(2- CF2Cl Methylphenyl) 302 CH2-(3- CF2ClMethylphenyl) 303 CH2-(4- CF2Cl Methylphenyl) 304 CH2-(2- CF2ClMethoxylphenyl) 305 CH2-(3- CF2Cl Methoxylphenyl) 306 CH2-(4- CF2ClMethoxylphenyl) 307 CH2-(2- CF2Cl fluorolphenyl) 308 CH2-(3- CF2Clfluorolphenyl) 309 CH2-(4- CF2Cl fluorolphenyl) Table 26 310 CH2-(2-CF2Cl Chlorophenyl) 311 CH2-(3- CF2Cl Chlorophenyl) 312 CH2-(4- CF2ClChlorophenyl) 313 CH2-(2- CF2Cl Bromophenyl) 314 CH2-(3- CF2ClBromophenyl) 315 CH2-(4- CF2Cl Bromophenyl) 316 CH2-(2- CF2Cliodophenyl) 317 CH2-(3- CF2Cl iodophenyl) 318 CH2-(4- CF2Cl iodophenyl)319 CH2-(1- CF2Cl naphthalenyl) 320 CH2-(2- CF2Cl naphthalenyl) 321naphthalen-1- CF2Cl ylmethyl 322 naphthalen-2- CF2Cl ylmethyl 323quinolin-2- CF2Cl ylmethyl 324 quinolin-7- CF2Cl ylmethyl 325isoquinolin- CF2Cl 7-ylmethyl 326 isoquinolin- CF2Cl 6-ylmethyl 327quinolin-6- CF2Cl ylmethyl 328 quinolin-3- CF2Cl ylmethyl 329isoquinolin- CF2Cl 3-ylmethyl 330 isoquinolin- CF2Cl 1-ylmethyl 331isoquinolin- CF2Cl 4-ylmethyl 332 quinolin-4- CF2Cl ylmethyl 333quinolin-5- CF2Cl ylmethyl 334 isoquinolin- CF2Cl 5-ylmethyl 335isoquinolin- CF2Cl 8-ylmethyl 336 quinolin-8- CF2Cl ylmethyl 337CH2O-Phenyl CF2Cl 338 CH2CH2O- CF2Cl Phenyl 339 2-pyridyl CF2Cl 3403-pyridyl CF2Cl 341 4-pyridyl CF2Cl 342 CH2-(2-pyridyl) CF2Cl 343CH2-(3-pyridyl) CF2Cl 344 CH2-(4-Chloro-3- CF2Cl pyridyl) 345CH2-(4-pyridyl) CF2Cl 346 CH2-(2-thienyl) CF2Cl 347 CH2-(3-thienyl)CF2Cl 348 CH2-(2-furanyl) CF2Cl 349 CH2-(3-furanyl) CF2Cl 350 CH2-(2-CF2Cl tetrahydrofuranyl) 351 CH2-(3- CF2Cl tetrahydrofuranyl) 352(1H-imidazol-2- CF2Cl yl)methyl 353 (1H-imidazol-1- CF2Cl yl)methyl 354(1H-imidazol-4- CF2Cl yl)methyl 355 CH2-(2- CF2Cl thiazolyl) 356 CH2-(3-CF2Cl thiazolyl) 357 CH2-(2- CF2Cl pyrrolyl) 358 CH2-(3- CF2Cl pyrrolyl)359 CH2-(1- CF2Cl pyrazolyl) 360 CH2-(2- CF2Cl pyrazolyl) 361 CH2-(3-CF2Cl pyrazolyl) 362 CH2-(4- CF2Cl pyrazolyl) 363 CH2-(5- CF2Clpyrazolyl) Table 27 364 CH2-(5- CF2Cl pyrazolyl) 365 CH2-(2- CF2Cloxazolyl) 366 CH2-(3- CF2Cl oxazolyl 367 CH2-(3- CF2Cl isoxazolyl) 368CH2-(4- CF2Cl isoxazolyl) 369 CH2-(5- CF2Cl isoxazolyl) 370 CH2CH2OCH3CF2Cl 371 CH2CH2OCH2CH3 CF2Cl 372 CH2CH2CH2OCH3 CF2Cl 373CH2CH2CH2OCH2CH3 CF2Cl 374 CH2CH2SCH3 CF2Cl 375 CH2CH2SCH2CH3 CF2Cl 376CH2CH2CH2SCH3 CF2Cl 377 CH2CH2CH2SCH2CH3 CF2Cl 378 Me CF2CF3 379 EtCF2CF3 380 n-Pr CF2CF3 381 i-Pr CF2CF3 382 t-Bu CF2CF3 383 n-Bu CF2CF3384 n-Pentyl CF2CF3 385 n-Hexyl CF2CF3 386 cyclopropyl CF2CF3 387cyclobutyl CF2CF3 388 cyclopentyl CF2CF3 389 cyclohexyl CF2CF3 390CH═CH2 CF2CF3 391 CH2CH═CH2 CF2CF3 392 CH2C≡CH CF2CF3 393 CH2CH2C≡CHCF2CF3 394 CH2CHF2 CF2CF3 395 CH2CCF3 CF2CF3 396 CH2CH2Cl CF2CF3 397CH2CHCl2 CF2CF3 398 2-fluoro-2- CF2CF3 chloroethyl 399 CH2CCl3 CF2CF3400 CH2CH2CN CF2CF3 401 CH2CH2CH2CN CF2CF3 402 CH2CH(CN)CH2CN CF2CF3 403CH2CH2OH CF2CF3 404 CH2CH2CH2OH CF2CF3 405 CH2CH(OH)CH2OH CF2CF3 406CH2CH2NO2 CF2CF3 407 Phenyl CF2CF3 408 CH2-Phenyl CF2CF3 409CH(Me)-Phenyl CF2CF3 410 C(Me2)-Phenyl CF2CF3 411 C(cyclopropyl)- CF2CF3Phenyl 412 CH2CH2-Phenyl CF2CF3 413 CH2-(2- CF2CF3 Methylphenyl) 414CH2-(3- CF2CF3 Methylphenyl) 415 CH2-(4- CF2CF3 Methylphenyl) 416CH2-(2- CF2CF3 Methoxylphenyl) 417 CH2-(3- CF2CF3 Methoxylphenyl) 418CH2-(4- CF2CF3 Methoxylphenyl) Table 28 419 CH2-(2- CF2CF3fluorolphenyl) 420 CH2-(3- CF2CF3 fluorolphenyl) 421 CH2-(4- CF2CF3fluorolphenyl) 422 CH2-(2- CF2CF3 Chlorophenyl) 423 CH2-(3- CF2CF3Chlorophenyl) 424 CH2-(4- CF2CF3 Chlorophenyl) 425 CH2-(2- CF2CF3Bromophenyl) 426 CH2-(3- CF2CF3 Bromophenyl) 427 CH2-(4- CF2CF3Bromophenyl) 428 CH2-(2- CF2CF3 iodophenyl) 429 CH2-(3- CF2CF3iodophenyl) 430 CH2-(4- CF2CF3 iodophenyl) 431 CH2-(1- CF2CF3naphthalenyl) 432 CH2-(2- CF2CF3 naphthalenyl) 433 naphthalen-1- CF2CF3ylmethyl 434 naphthalen-2- CF2CF3 ylmethyl 435 quinolin-2- CF2CF3ylmethyl 436 quinolin-7- CF2CF3 ylmethyl 437 isoquinolin- CF2CF37-ylmethyl 438 isoquinolin- CF2CF3 6-ylmethyl 439 quinolin-6- CF2CF3ylmethyl 440 quinolin-3- CF2CF3 ylmethyl 441 isoquinolin- CF2CF33-ylmethyl 442 isoquinolin- CF2CF3 1-ylmethyl 443 isoquinolin- CF2CF34-ylmethyl 444 quinolin-4- CF2CF3 ylmethyl 445 quinolin-5- CF2CF3ylmethyl 446 isoquinolin- CF2CF3 5-ylmethyl 447 isoquinolin- CF2CF38-ylmethyl 448 quinolin-8- CF2CF3 ylmethyl 449 CH2O-Phenyl CF2CF3 450CH2CH2O-Phenyl CF2CF3 451 2-pyridyl CF2CF3 452 3-pyridyl CF2CF3 4534-pyridyl CF2CF3 454 CH2-(2-pyridyl) CF2CF3 455 CH2-(3-pyridyl) CF2CF3456 CH2-(4-Chloro-3- CF2CF3 pyridyl) 457 CH2-(4-pyridyl) CF2CF3 458CH2-(2-thienyl) CF2CF3 459 CH2-(3-thienyl) CF2CF3 460 CH2-(2-furanyl)CF2CF3 461 CH2-(3-furanyl) CF2CF3 462 CH2-(2- CF2CF3 tetrahydrofuranyl)463 CH2-(3- CF2CF3 tetrahydrofuranyl) 464 (1H-imidazol-2- CF2CF3yl)methyl 465 (1H-imidazol-1- CF2CF3 yImethyl 466 (1H-imidazol-4- CF2CF3yl)methyl 467 CH2-(2- CF2CF3 thiazolyl) 468 CH2-(3- CF2CF3 thiazolyl)469 CH2-(2- CF2CF3 pyrrolyl) 470 CH2-(3- CF2CF3 pyrrolyl) 471 CH2-(5-CF2CF3 methylpyrazolyl-1-yl) 472 CH2-(1- CF2CF3 pyrazolyl) Table 29 473CH2-(2- CF2CF3 pyrazolyl) 474 CH2-(3- CF2CF3 pyrazolyl) 475 CH2-(4-CF2CF3 pyrazolyl) 476 CH2-(5- CF2CF3 pyrazolyl) 477 CH2-(2- CF2CF3oxazolyl) 478 CH2-(3- CF2CF3 oxazolyl 479 CH2-(3- CF2CF3 isoxazolyl) 480CH2-(4- CF2CF3 isoxazolyl) 481 CH2-(5- CF2CF3 isoxazolyl) 482 CH2CH2OCH3CF2CF3 483 CH2CH2OCH2CH3 CF2CF3 484 CH2CH2CH2OCH3 CF2CF3 485CH2CH2CH2OCH2CH3 CF2CF3 486 CH2CH2SCH3 CF2CF3 487 CH2CH2SCH2CH3 CF2CF3488 CH2CH2CH2SCH3 CF2CF3 489 CH2CH2CH2SCH2CH3 CF2CF3 490 Me CF2CF3 491Et CH2Cl 492 n-Pr CHCl2 493 i-Pr CCl3 494 t-Bu CHClBr 495 n-Bu CHBr2 496n-Pentyl CH═CH2 497 n-Hexyl CH2CH═CH2 498 cyclopropyl CH2C≡CH

R6 R7 499 H CF3 500 Me CF3 501 Et CF3 502 n-Pr CF3 503 i-Pr CF3 504 t-BuCF3 505 cyclopropyl CF3 506 CH═CH2 CF3 507 CH2CH═CH2 CF3 508 CH2C≡CH CF3509 Ph CF3 510 CH2Ph CF3 511 COMe CF3 512 COEt CF3 513 CO-n-Pr CF3 514CO-i-Pr CF3 515 CO-cyclopropyl CF3 516 COCH═CH2 CF3 517 COCH2CH═CH2 CF3518 COCH2C≡CH CF3 519 COPh CF3 520 CO-(2-pyridyl) CF3 Table 30 521CO-(3-pyridyl) CF3 522 CO-(4-pyridyl) CF3 523 COOMe CF3 524 COOEt CF3525 COO-i-Pr CF3 526 COO-t-Bu CF3 527 COOPh CF3 528 SO2Me CF3 529 SO2EtCF3 530 SO2Ph CF3 531 SO2-(4- CF3 methylphenyl) 532 NHMe CF3 533 NHEtCF3 534 NH-n-Pr CF3 535 NHCH2CH2Cl CF3 536 NHCH2Ph CF3 537 N(Me)2 CF3538 Me CHF2 539 Et CHF2 540 n-Pr CHF2 541 i-Pr CHF2 542 t-Bu CHF2 543cyclopropyl CHF2 544 CH═CH2 CHF2 545 CH2CH═CH2 CHF2 546 CH2C≡CH CHF2 547Ph CHF2 548 CH2Ph CHF2 549 COMe CHF2 550 COEt CHF2 551 CO-n-Pr CHF2 552CO-i-Pr CHF2 553 CO-cyclopropyl CHF2 554 COCH═CH2 CHF2 555 COCH2CH═CH2CHF2 556 COCH2C≡CH CHF2 557 COPh CHF2 558 CO-(2-pyridyl) CHF2 559CO-(3-pyridyl) CHF2 560 CO-(4-pyridyl) CHF2 561 COOMe CHF2 562 COOEtCHF2 563 COO-i-Pr CHF2 564 COO-t-Bu CHF2 565 COOPh CHF2 566 SO2Me CHF2567 SO2Et CHF2 568 SO2Ph CHF2 569 SO2-(4- CHF2 methylphenyl) 570 MeCF2Cl 571 Et CF2Cl 572 n-Pr CF2Cl 573 i-Pr CF2Cl 574 t-Bu CF2Cl Table 31575 cyclopropyl CF2Cl 576 CH═CH2 CF2Cl 577 CH2CH═CH2 CF2Cl 578 CH2C≡CHCF2Cl 579 Ph CF2Cl 580 CH2Ph CF2Cl 581 COMe CF2Cl 582 COEt CF2Cl 583CO-n-Pr CF2Cl 584 CO-i-Pr CF2Cl 585 CO-cyclopropyl CF2Cl 586 COCH═CH2CF2Cl 587 COCH2CH═CH2 CF2Cl 588 COCH2C≡CH CF2Cl 589 COPh CF2Cl 590CO-(2-pyridyl) CF2Cl 591 CO-(3-pyridyl) CF2Cl 592 CO-(4-pyridyl) CF2Cl593 COOMe CF2Cl 594 COOEt CF2Cl 595 COO-i-Pr CF2Cl 596 COO-t-Bu CF2Cl597 COOPh CF2Cl 598 SO2Me CF2Cl 599 SO2Et CF2Cl 600 SO2Ph CF2Cl 601SO2-(4- CF2Cl methylphenyl) 602 Me CF2CF3 603 Et CF2CF3 604 n-Pr CF2CF3605 i-Pr CF2CF3 606 t-Bu CF2CF3 607 cyclopropyl CF2CF3 608 CH═CH2 CF2CF3609 CH2CH═CH2 CF2CF3 610 CH2C≡CH CF2CF3 611 Ph CF2CF3 612 CH2Ph CF2CF3613 COMe CF2CF3 614 COEt CF2CF3 615 CO-n-Pr CF2CF3 616 CO-i-Pr CF2CF3617 CO-cyclopropyl CF2CF3 618 COCH═CH2 CF2CF3 619 COCH2CH═CH2 CF2CF3 620COCH2C≡CH CF2CF3 621 COPh CF2CF3 622 CO-(2-pyridyl) CF2CF3 623CO-(3-pyridyl) CF2CF3 624 CO-(4-pyridyl) CF2CF3 625 COOMe CF2CF3 626COOEt CF2CF3 627 COO-i-Pr CF2CF3 Table 32 628 COO-t-Bu CF2CF3 629 COOPhCF2CF3 630 SO2Me CF2CF3 631 SO2Et CF2CF3 632 SO2Ph CF2CF3 633 SO2-(4-CF2CF3 methylphenyl) 634 Me CF2CF3 635 Et CH2Cl 636 n-Pr CHCl2 637 i-PrCCl3 638 t-Bu CHClBr 639 cyclopropyl CHBr2 640 CH═CH2 CH═CH2 641CH2CH═CH2 CH2CH═CH2 642 CH2C≡CH CH2C≡CH Table 33 R

R1 643 C6F5 644 CH2OCH2C6H5

R2 645 CH2C6H5 646 isopropyl 647 CH2CH2CH═CH2

R3 648 C6F5 649 CH2OCH2C6H5 Table 34 R

R4 R5 650 Ethyl CH2CF3 651 n-Propyl CH2CF3 652 iso-Propyl CH2CF3 653t-Butyl CH2CF3 654 n-Butyl CH2CF3 655 cyclopropyl CH2CF3 656 cyclopentylCH2CF3 657 cyclohexyl CH2CF3 658 n-hexa decyl CF3 659 n-tridecyl CF3 660CH(CH3)CH2CH3 CF3 661 CH(CH3)CH2CH2CH3 CF3 662 CH(CH3)-isopropyl CF3 6631-phenylethyl CF3 664 1,2,3,4- CF3 tetrahydronaphthalen- 1-yl 6651-(naphthalen-1- CF3 yl)ethyl 666 1-(naphthalen-1- CF3 yl)propyl 6671-(furan-2- CF3 yl)ethyl 668 3.3-dimethylbutan- CF3 2-yl 6691-(thiophen-2- CF3 yl)ethyl 670 CH2CH2F CF3 671 n-Octyl CF3 672 n-OctylCHF2 673 n-Octyl CF2Cl 674 n-Octyl CF2CF3 675 n-Octyl CF2CF3 676CH(C6H5)2 CF3 677 CH(C6H5)2 CHF2 678 CH(C6H5)2 CF2Cl 679 CH(C6H5)2CF2CF3 680 CH(C6H5)2 CF2CF3 681 CH(CH2CH3)2 CF3 682 CH(CH2CH3)2 CHF2 683CH(CH2CH3)2 CF2Cl 684 CH(CH2CH3)2 CF2CF3 685 CH(CH2CH3)2 CF2CF3 686CH(CH2CH2CH3)2 CF3 687 CH(CH2CH2CH3)2 CHF2 688 CH(CH2CH2CH3)2 CF2Cl 689CH(CH2CH2CH3)2 CF2CF3 690 CH(CH2CH2CH3)2 CF2CF3 Table 35 R

Y1 Y2 Ry 691 O O Methyl 692 O O Ethyl 693 O O Propyl 694 O O isopropyl695 S O Methyl 696 S O Ethyl 697 S O Propyl 698 S O isopropyl 699 S SMethyl 700 S S Ethyl 701 S S Propyl 702 S S isopropyl

n Rz 703 1 CF3 704 1 CF2CF3 705 1 CH2CF3 706 1 Me 707 2 CF3 708 2 CF2CF3709 2 CH2CF3 710 2 Me

Examples of preferred compounds of Formula (I) include compounds shownin the following Tables.

TABLE 36 Compound No Ar A Y R 266-2   6-Chloro-3- A-38 H COCF3 pyridyl444-2   2-chloro-5- A-38 H COCF3 thiazolyl 190-2   6-Chloro-3- A-13 HCOCF3 pyridyl 201-2   6-Chloro-3- A-14 H COCF3 pyridyl 223-2  6-Chloro-3- A-16 H COCF3 pyridyl 146-2   6-Chloro-3- A-1 3-OH COCF3pyridyl 224-2   2-chloro-5- A-16 H COCF3 thiazolyl 102-2   6-Chloro-3-A-1 3-CN COCF3 pyridyl 212-2   6-Chloro-3- A-15 H COCF3 pyridyl 1-206-Chloro-3- A-1 H CSCF3 pyridyl 12-2  2-Chloro-4- A-1 H COCF3 pyridyl213-2   2-chloro-5- A-15 H COCF3 thiazolyl 1-17 6-Chloro-3- A-1 HCOOCH2CF3 pyridyl 1-18 6-Chloro-3- A-1 H COOCH(Me)CF3 pyridyl 1-196-Chloro-3- A-1 H COOCH(CF3)2 pyridyl 7-2  5- A-1 H COCF3 Chloropyrazin-2-yl 1-13 6-Chloro-3- A-1 H COCH2CF3 pyridyl 168-2   6-Chloro-3- A-15-OH COCF3 pyridyl 1-21 6-Chloro-3- A-1 H CSCHF2 pyridyl 3-206-Fluoro-3- A-1 H CSCF3 pyridyl 4-20 6-Bromo-3- A-1 H CSCF3 pyridyl 3-3 6-Fluoro-3- A-1 H COCHF2 pyridyl 4-3  6-Bromo-3- A-1 H COCHF2 pyridyl5-5  6-Chloro-5- A-1 H COCF2CF3 fluoro-3-pyridyl 6-5  2-Chloro-5- A-1 HCOCF2CF3 pyrimidinyl 1-22 6-Chloro-3- A-1 H CSCF2Cl pyridyl 1-236-Chloro-3- A-1 H CSCF2CF3 pyridyl 5-20 6-Chloro-5- A-1 H CSCF3fluoro-3-pyridyl 5-3  6-Chloro-5- A-1 H COCHF2 fluoro-3-pyridyl 6-3 2-Chloro-5- A-1 H COCHF2 pyrimidinyl 8-2  6- A-1 H COCF3Chloropyridazin- 3-yl 5-4  6-Chloro-5- A-1 H COCF2Cl fluoro-3-pyridyl4-4  6-Bromo-3- A-1 H COCF2Cl pyridyl 6-4  2-Chloro-5- A-1 H COCF2Clpyrimidinyl 4-5  6-Bromo-3- A-1 H COCF2CF3 pyridyl 2-20 2-chloro-5- A-1H CSCF3 thiazolyl 10-20  6- A-1 H CSCF3 trifluoromethyl- 3-pyridyl 3-4 6-Fluoro-3- A-1 H COCF2Cl pyridyl 3-5  6-Fluoro-3- A-1 H COCF2CF3pyridyl 11-20  3-THF A-1 H CSCF3 1-14 6-Chloro-3- A-1 H COCH═CH2 pyridyl1-37 6-Chloro-3- A-1 H CSEt pyridyl 1-39 6-Chloro-3- A-1 H CS-i-Prpyridyl 1-40 6-Chloro-3- A-1 H CS-cyclopropyl pyridyl 1-15 6-Chloro-3-A-1 H COCH2CΞCH pyridyl 1-35 6-Chloro-3- A-1 H CSCH2CH2Ph pyridyl  1-5016-Chloro-3- A-1 H C(═NOEt)CF3 pyridyl  1-499 6-Chloro-3- A-1 HC(═NOH)CF3 pyridyl  1-510 6-Chloro-3- A-1 H C(═NOCH2Ph)CF3 pyridyl 1-511 6-Chloro-3- A-1 H C(═NOCOMe)CF3 pyridyl  1-519 6-Chloro-3- A-1 HC(═NOCOPh)CF3 pyridyl  1-523 6-Chloro-3- A-1 H C(═NOCOOMe)CF3 pyridyl

TABLE 37 Com- pound No Ar A Y R 1-528 6-Chloro-3- A-1 H C(═NOSO2Me)CF3pyridyl 1-531 6-Chloro-3- A-1 H C(═NOSO2-(4- pyridyl Methylphenyl))CF31-507 6-Chloro-3- A-1 H C(═NOCH2CH═CH2)CF3 pyridyl 1-516 6-Chloro-3- A-1H C(═NOCOCH═CH2)CF3 pyridyl 1-518 6-Chloro-3- A-1 H C(═NOCOCH2C≡CH)CF3pyridyl 1-527 6-Chloro-3- A-1 H C(═NOCOOPh)CF3 pyridyl 1-521 6-Chloro-3-A-1 H C(═NOCO-3-pyr)CF3 pyridyl 1-43  6-Chloro-3- A-1 H C(═NEt)CF3pyridyl 1-536 6-Chloro-3- A-1 H C(═NOCONHCH2Ph)CF3 pyridyl 1-42 6-Chloro-3- A-1 H C(═NMe)CF3 pyridyl 1-500 6-Chloro-3- A-1 H C(═NOMe)CF3pyridyl 1-504 6-Chloro-3- A-1 H C(═NOtBu)CF3 pyridyl 1-534 6-Chloro-3-A-1 H C(═NOCONHnPr)CF3 pyridyl 1-535 6-Chloro-3- A-1 HC(═NOCONHCH2CH2Cl)CF3 pyridyl 1-72  6-Chloro-3- A-1 H C(═NCH2Ph)CF3pyridyl 1-150 6-Chloro-3- A-1 H C(═NCH2CH2SMe)CF3 pyridyl 1-67 6-Chloro-3- A-1 H C(═NCH2CH2OH) pyridyl 1-515 6-Chloro-3- A-1 HC(═NOCO-cyclopropyl)CF3 pyridyl 1-56  6-Chloro-3- A-1 H C(═NCH2C ΞCH)CF3 pyridyl 1-512 6-Chloro-3- A-1 H C(═NOCOCH2CH3)CF3 pyridyl 1-5146-Chloro-3- A-1 H C(═NOCOiPr)CF3 pyridyl 1-50  6-Chloro-3- A-1 HC(═N-cyclopropyl)CF3 pyridyl 1-114 6-Chloro-3- A-1 H C(═NCH2CH2OPh)CF3pyridyl 1-44  6-Chloro-3- A-1 H C(═N-n-Pr)CF3 pyridyl 1-118 6-Chloro-3-A-1 H C(═NCH2-(2-pyridyl))CF3 pyridyl 1-119 6-Chloro-3- A-1 HC(═NCH2-(3-pyridyl))CF3 pyridyl 1-47  6-Chloro-3- A-1 H C(═N-n-Bu)CF3pyridyl 1-55  6-Chloro-3- A-1 H C(═N—CH2CH═CH2)CF3 pyridyl 1-1226-Chloro-3- A-1 H C(═NCH2-(2-thienyl))CF3 pyridyl 1-45  6-Chloro-3- A-1H C(═N-i-Pr)CF3 pyridyl 1-124 6-Chloro-3- A-1 H C(═NCH2-(2-furanyl))CF3pyridyl 1-126 6-Chloro-3- A-1 H C(═NCH2-(2- pyridyltetrahydrofuranyl))CF3 1-64  6-Chloro-3- A-1 H C(═NCH2CN)CF3 pyridyl1-146 6-Chloro-3- A-1 H C(═NCH2CH2OCH3)CF3 pyridyl 1-52  6-Chloro-3- A-1H C(═N-cyclopentyl)CF3 pyridyl 1-121 6-Chloro-3- A-1 HC(═NCH2-(4-pyridyl))CF3 pyridyl 1-53  6~Chloro-3- A-1 HC(═N-cyclohexyl)CF3 pyridyl 1-76  6-Chloro-3- A-1 H C(═NCH2CH2Ph)CF3pyridyl 267-2   6-Chloro-3- A-39 H COCF3 pyridyl 253-2   6-Chloro-3-A-25 H COCF3 pyridyl 251-2   6-Chloro-3- A-23 H COCF3 pyridyl 13-2   3-A-1 H COCF3 Cyanophenyl 1-1  6-Chloro-3- A-1 H CHO pyridyl 1-41 6-Chloro-3- A-1 H C(═NH)CF3 pyridyl

TABLE 38 Compound No. Ar A Y R 1-647 6-Chloro-3-pyridyl A-1 HCOOCH2CH2CH═CH2 1-670 6-Chloro-3-pyridyl A-1 H C(═NCH2CH2F)CF3 157-2  6-Chloro-3-pyridyl A-1 4-OH COCF3 1-10  6-Chloro-3-pyridyl A-1 HCO(2,2-difluonocyclopropyl) 580-2   6-chloro-3-pyridyl-N-oxid A-1 HCOCF3 1-671 6-Chloro-3-pyridyl A-1 H C(═N(CH2)7CH3)CF3 1-6586-Chloro-3-pyridyl A-1 H C(═N(CH2)15CH3)CF3 1-659 6-Chloro-3-pyridyl A-1H C(═N(CH2)11CH3)CF3 1-660 6-Chloro-3-pyridyl A-1 HC(═NCH(CH3)CH2CH3)CF3 1-681 6-Chloro-3-pyridyl A-1 H C(═NCH(CH2CH3)2)CF31-686 6-Chloro-3-pyridyl A-1 H C(═NCH(CH2CH2CH3)2)CF3 1-6616-Chloro-3-pyridyl A-1 H C(═NCH(CH3)CH2CH2CH3)CF3 1-6626-Chloro-3-pyridyl A-1 H C(═NCH(iso-propyl)CH3)CF3 1-6636-Chloro-3-pyridyl A-1 H C(═N(1-phenylethyl))CF3 1-6646-Chloro-3-pyridyl A-1 H C(═N(1,2,3,4-tetrahydronaphthalen-1-yl)CF31-665 6-Chloro-3-pyridyl A-1 H C(═N(1-(naphthalen-1-yl)ethyl))CF3 1-6666-Chloro-3-pyridyl A-1 H C(═N(1-(naphthalen-1-yl)propyl))CF3 1-6676-Chloro-3-pyridyl A-1 H C(═N(1-(furan-2-yl)ethyl))CF3 1-6766-Chloro-3-pyridyl A-1 H C(═NCH(C6H5)2)CF3 1-668 6-Chloro-3-pyridyl A-1H C(═N(3,3-dimethylbutan-2-yl))CF3 47-2   6-Chloro-3-pyridyl A-1 6-FCOCF3 91-2   6-Chloro-3-pyridyl A-1 6-Cl COCF3 478-2  6-Chloro-3-pyridyl A-1 6-CH3 COCF3 479-2   2-Chloro-5-thiazolyl A-16-CH3 COCF3 1-51  6-Chloro-3-pyridyl A-1 H C(═N-cyclobutyl)CF3 566-2  6-Chloro-3-pyridyl A-1 6-CH3O COCF3 488-2   3-tetrahydrofuranyl A-16-CH3 COCF3 511-2   6-Chloro-3-pyridyl A-1 5-NO2 COCF3 1-6696-Chloro-3-pyridyl A-1 H C(═N(1-(thiophen-2-yl)ethyl))CF3 179-2  6-Chloro-3-pyridyl A-1 6-OH COCF3 (also represents a tautomer) 555-2  6-Chloro-3-pyridyl A-1 5-OCH3 COCF3 577-2   2,6-dichrolo-3-pyridyl A-1 HCOCF3 544-2   6-Chloro-3-pyridyl A-1 4-OCH3 COCF3 168-2  6-Chloro-3-pyridyl A-1 5-OH COCF3 1-644 6-Chloro-3-pyridyl A-1 HCOCH2OCH2C6H5 578-644  3-pyridyl A-1 H COCH2OCH2C6H5 1-7036-Chloro-3-pyridyl A-1 H SOCF3 1-707 6-Chloro-3-pyridyl A-1 H SO2CF31-706 6-Chloro-3-pyridyl A-1 H SOCH3 1-692 6-Chloro-3-pyridyl A-1 HP(═O)(OEt)2 1-700 6-Chloro-3-pyridyl A-1 H P(═S)(SEt)2 1-7016-Chloro-3-pyridyl A-1 H P(═S)(S-n-propyl)2 1-702 6-Chloro-3-pyridyl A-1H P(═S)(S-isopropyl)2 1-646 6-Chloro-3-pyridyl A-1 H COO-iso-Pr 1-6456-Chloro-3-pyridyl A-1 H COOCH2C6H5 1-643 6-Chloro-3-pyridyl A-1 HCOC6F5 2-643 2-Chloro-5-thiazolyl A-1 H COC6F5

TABLE 39

Compound No. Ar R1a Y P212 6-chloro-3- CF3 H pyridyl P213 2-chloro-5-CF3 H thiazolyl P214 6-chloro-3- OCH3 H pyridyl P215 6-chloro-3- CF3 5-pyridyl Cl P216 6-chloro-3- CF3 5- pyridyl F P217 6-chloro-3- CF3 4-pyridyl Cl P218 2-chloro-5- CF3 5- thiazolyl Cl P219 2-chloro-5- CF3 5-thiazolyl F P220 2-chloro-5- CF3 4- thiazolyl Cl P221 6-chloro-3- CF3 3-pyridyl Me P222 6-chloro-3- CF3 4- pyridyl Me P223 6-chloro-3- CF3 5-pyridyl Me P224 phenyl CF3 H P225 4-chlorophenyl CF3 H P226 3-pyridylCF3 H P227 6-chloro-5- CF3 H fluoro-3-pyridyl P228 6- CF3 Htrifluoromethyl- 3-pyridyl P229 6-fluoro-3- CF3 H pyridyl P2305,6-dichloro-3- CF3 H pyridyl P231 6-bromo-3- CF3 H pyridyl P2326-chloro-3- CF3 4- pyridyl F P233 6-chloro-3- CF3 3- pyridyl F P2346-chloro-3- CHCl2 H pyridyl P235 6-chloro-3- CCl3 H pyridyl P2366-chloro-3- CH2Cl H pyridyl P238 6-chloro-3- CHF2 H pyridyl P2396-chloro-3- CF2Cl H pyridyl P240 6-chloro-3- CHClBr H pyridyl P2416-chloro-3- CHBr2 H pyridyl P242 6-chloro-3- CF2CF3 H pyridyl P2432-chloro-5- CF3 H pyrimidinyl P244 6-chloro-3- CH2Br H pyridyl

Examples of more preferred compounds include

-   N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide    (Compound P212) and-   N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide    (Compound 1-20),    N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide    (Compound 1-45).

In addition, in the present invention, an acid addition salt of a noveliminopyridine derivative represented by Formula (I) (preferably, anagriculturally and zootechnically acceptable acid addition salt) mayalso be used, and examples thereof include an acid addition salt such ashydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

The novel iminopyridine derivative represented by Formula (I) itselfshows excellent pest control effects against pest insects, and is mixedand used with other pest control agents, thereby showing excellent pestcontrol effects compared to when a single agent is used. Therefore, thepresent invention provides a pest control composition prepared bycontaining at least one of novel iminopyridine derivatives representedby Formula (I) and at least one of other pest control agents.Furthermore, the present invention provides an excellent pest controlcomposition prepared by containing at least one of novel iminopyridinederivatives represented by Formula (I) and at least one of otherinsecticides and/or fungicides.

Examples of a pest control composition provided by the present inventioninclude a pest control agent for agricultural and horticultural, acontrol agent for animal parasitic pests, an agent for controllinghygiene pests, an agent for controlling nuisance pests, an agent forcontrolling stored grain and stored product pests, an agent forcontrolling house pests and the like, preferred examples thereof includea pest control agent for agricultural and horticultural and a controlagent for animal parasitic pests.

Examples of the insect species against which a pest control compositioncontaining a novel iminopyridine derivative represented by Formula (I)or at least one of acid addition salts thereof, and at least one ofother pest control agents shows pest control effects includelepidopteran pests (for example, Spodoptera litura, cabbage armyworm,Mythimna separata, cabbageworm, cabbage moth, Spodoptera exigua, ricestem borer, grass leaf roller, tortricid, codling moth, leafminer moth,tussock moth, Agrotis spp), Helicoverpa spp, Heliothis spp and thelike), hemipteran pests (for example, aphids (Aphididae, Adelgidae,Phylloxeridae) such as Myzus persicae, Aphis gossypii, Aphis fabae, cornleaf aphid, pea aphid, Aulacorthum solani, Aphis craccivora, Macrosiphumeuphorbiae, Macrosiphum avenae, Methopolophium dirhodum, Rhopalosiphumpadi, greenbug, Brevicoryne brassicae, Lipaphis erysimi, Aphiscitricola, Rosy apple aphid, apple blight, Toxoptera aurantii andToxoptera citricidus, leafhoppers such as Nephotettix cincticeps andEmpoasca vitis, planthoppers such as Laodelphax striatellus, Nilaparvatalugens and Sogatella furcifera, Pentatomorpha such as Eysarcorisventralis, Nezara viridula and Trigonotylus coelestialium, whiteflies(Aleyrodidae) such as silverleaf whitefly, Bemisia tabaci and greenhousewhitefly, and scale insects (Diaspididae, Margarodidae, Ortheziidae,Aclerdiae, Dactylopiidae, Kerridae, Pseudococcidae, Coccidae,Eriococcidae, Asterolecaniidae, Beesonidae, Lecanodiaspididae,Cerococcidae and the like) such as Pseudococcus comstocki, Planococcuscitri, Pseudaulacaspis pentagona and Aonidiella aurantii), coleopteranpests (for example, Lissorhoptrus oryzophilus, Callosobruchus chinensis,Tenebrio molitor, Diabrotica virgifera virgifera, Diabroticaundecimpunctata howardi, Anomala cuprea, Anomala rufocuprea, Phyllotretastriolata, Aulacophora femoralis, Leptinotarsa decemlineata, Oulemaoryzae, Bostrichidae, Cerambycidae and the like), Acarina (for example,Tetranychus urticae, Tetranychus kanzawai, Panonychus citri and thelike), hymenopteran pests (for example, Tenthredinidae), orthopteranpests (for example, Acridioidea), dipteran pests (for example,Agromyzidae), thysanopteran pests (for example, Thrips palmi,Frankliniella occidentalis and the like), phytoparasitic nematode (forexample, Meloidogyne, Pratylenchus, Aphelenchoides besseyi,Bursaphelenchus xylophilus and the like), and the like, examples ofzooparasites include Ixodidae (for example, Amblyomma americanum,Amblyomma maculatum, Boophilus microplus, Dermacentor andersoni,Dermacentor occidentalis, Dermacentor variabilis, Haemaphysaliscampanulata, Haemaphysalis flava, Haemaphysalis longicornis,Haemaphysalis megaspinosa Saito, Ixodes nipponensis, Ixodes ovatus,Ixodes pacifcus, Ixodes persulcatus, Ixodes ricinus, Ixodes scapularis,Ornithodoros moubata pacifcus and Rhipicephalus sanguineus), Cheyletidae(for example, Cheyletiella blakei and Cheyletiella yasguri), Demodex(for example, Demodex canis and Demodex cati), Psoroptidae (for example,Psoroptes communis), Sarcoptidae (for example, Chorioptes bovis andOtodectes cynotis), Dermanyssidae (for example, Ornithonyssussylviarum), Dermanyssus gallinae, Pterolichus (for example, Megniniacubitalis and Pterolichus obtusus), Trombiculidae (for example,Helenicula miyagawai and Leptotrombidium akamushi), Shiphonaptera (forexample, Ctenocephalides felis, Pulex irritans, Xenopsylla cheopis andXenopsylla), Mallophaga (for example, Trichodectes canis and Menopongallinae), Anoplura (for example, Haematopinus suis, Linognathussetosus, Pediculus humanus humanus, Pediculus humanus, Pthirus pubis andCimex lectularius), Diptera (for example, Musca domestica, Hypodermabovis, Stomoxys calcitrans and Gasterophilus), Psychodidae (for example,Phlebotomus), Glossina morsitans, Tabanidae, Ormosia tokionis (forexample, Aedes albopictus and Aedes aegypti), Culicidae (for example,Culex pipiens pallens), Anophelini, Ceratopogonidae and the like),Simuliidae, Ceratopogonidae, Reduviidae, Monomorium pharaonic, Nematoda(for example, Strongyloides, Ancylostomatoidea, Strongyloidea (forexample, Haemonchus contortus and Nippostrongylus braziliensis),Trichostrongyloidea, Metastrongyloidea (for example, Metastrongyluselongatus, Angiostrongylus cantonensis and Aelurostrongylus abstrutus),Oxyuroidea, Haterakoidea (for example, Ascaridia galli), Ascaridoidea(for example, Anisakis simplex, Ascaris suum, Parascaris equorum,Toxocara canis and Toxocara cati), Spiruroidea (for example,Subuluroidea, Gnathostoma spinigerum, Physaloptea praeputialis, Ascaropsstrongylina, Draschia megastoma and Ascaria hamulosa, Dracunculusmedinensis), Filarioidea (for example, Dirofilaria immitis, lymphaticfilarial, Onchocerca volvulus and Loa loa), Dioctophymatoidea,Trichinella (for example, Trichuris vulpis and Trichinella spiralis),Trematoda (for example, Schistosoma japonicum and Fasciola hepatica),Acanthocephala, Taenia (for example, Pseudophyllidea (for example,Spirometra erinaceieuropaei) and Cyclophyllidea (for example, Dipylidiumcaninum)), Protozoa, and the like, and examples of hygiene pests includePeriplaneta (for example, Blattella germanica), Acaridae (for example,Tyrophagus putrescentiae), and Isoptera (for example, Coptotermesformosanus). Among them, preferred examples of an insect species, towhich the pest control agent of the present invention is applied,include lepidopteran pests, hemipteran pests, thysanopteran pests,dipteran pests, coleopteran pests, zooparasitic Shiphonaptera or Acari,Dirofilaria immitis, Periplaneta and Isoptera (for example, at least oneinsect species selected from the group consisting of cabbage moth,Spodoptera litura, Aphis gossypii, Myzus persicae, Laodelphaxstriatellus, Nilaparvata lugens, Sogatella furcifera, Nephotettixcincticeps, Frankliniella occidentalis, Aulacophora femoralis, Oulemaoryzae, Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Muscadomestica, Haemaphysalis longicornis, Dirofilaria immitis, Blattellagermanica and Coptotermes formosanus), and particularly preferredexamples thereof include cabbage moth, Aphis gossypii, Myzus persicae,Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera,Nephotettix cincticeps, Aulacophora femoralis, Oulema oryzae,Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Musca domesticaand Haemaphysalis longicornis.

In the present specification, examples of other pest control agentswhich may be mixed with the novel iminopyridine derivative representedby Formula (I) include an insecticide, a fungicide, a miticide, aherbicide, a plant growth regulator and a control agent for animalparasites, and examples of a specific chemical include those describedin The Pesticide Manual (13th edition and published by the British CropProtection Council) and the SHIBUYA INDEX (15th edition, 2010 andpublished by SHIBUYA INDEX RESEARCH GROUP).

Examples of other pest control agents which may be mixed with the noveliminopyridine derivative represented by Formula (I) preferably includean insecticide, a fungicide, a herbicide and a control agent for animalparasitic pests, and also those prepared by mixing a fungicide with aninsecticide.

Preferred examples of other pest control agents which may be mixed withthe novel iminopyridine derivative represented by Formula (I) include anorganic phosphoric ester compound, a carbamate-based compound, anereistoxin derivative, an organochlorine compound, a pyrethroid-basedcompound, a benzoyl urea-based compound, a juvenile hormone-likecompound, a molting hormone-like compound, a neonicotinoid-basedcompound, a sodium channel blocker for nerve cells, aninsecticidalmacrocyclic lactone, a γ-aminobutyric acid (GABA)antagonist, a ryanodine receptor agonistic compound, insecticidal ureas,a BT agent, an entomopathogenic viral agent and the like, as aninsecticide, and more preferred examples thereof include an organicphosphoric ester compound such as acephate, dichlorvos, EPN,fenitrothion, fenamifos, prothiofos, profenofos, pyraclofos,chlorpyrifos-methyl, diazinon, trichlorfon, tetrachlorvinphos,bromofenofos and cythioate, a carbamate-based compound such as methomyl,thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb,ethiofencarb, fenothiocarb, pirimicarb, carbofuran and benfuracarb, anereistoxin derivative such as cartap and thiocyclam, an organochlorinecompound such as dicofol and tetradifon, a pyrethroid-based compoundsuch as allethrin, d⋅d-T allethrin, dl⋅d-T80 allethrin, pyrethrins,phenothrin, flumethrin, cyfluthrin, d⋅d-T80 prarethrin, phthalthrin,transfluthrin, resmethrin, cyphenothrin, pyrethrum extract,synepirin222, synepirin500, permethrin, tefluthrin, cypermethrin,deltamethrin, cyhalothrin, fenvalerate, fluvalinate, ethofenprox andsilafluofen, a benzoyl urea-based compound such as diflubenzuron,teflubenzuron, flufenoxuron, chlorfluazuron and lufenuron, a juvenilehormone-like compound such as methoprene and a molting hormone-likecompound such as chromafenozide. In addition, examples of othercompounds include buprofezin, hexythiazox, amitraz, chlordimeform,pyridaben, fenpyroxymate, Pyrimidifen, tebufenpyrad, tolfenpyrad,acequinocyl, cyflumetofen, flubendizmide, ethiprole, fipronil,etoxazole, imidacloprid, clothianidin, thiamethoxam, acetamiprid,nitenpyram, thiacloprid, dinotefuran, pymetrozine, bifenazate,spirodiclofen, spiromesifen, spirotetramat, flonicamid, chlorfenapyr,pyriproxyfen, indoxacarb, pyridalyl, spinosad, spinetoram, avermectin,milbemycin, pyflubumide, cyenopyrafen, pyrifluquinazon,chlorantraniliprole, cyantraniliprole, lepimectin, metaflumizone,pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor,flupyradifurone, flometoquin, ivermectin, selamectin, moxidectin,doramectin, eprinomectin, milbemycin oxime, deet, metoxadiazon,cyromazine, triflumuron, star anise oil, triclabendazole, flubendazole,fenbendazole, antimony sodium gluconate, levamisole hydrochloride,bithionol, dichlorofen, phenothiazine, piperazine carbon bisulfide,piperazine phosphate, piperazine adipate, piperazine citrate,melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate,pyrantel, praziquantel, febantel, emodepside, emamectin benzoate,cycloxaprid,1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate,an organic metal-based compound, a dinitro-based compound, an organicsulfur compound, a urea-based compound, a triazine-based compound, ahydrazine-based compound, and a compound represented by the followingFormula (II) or agriculturally and zootechnically acceptable acidaddition salts thereof. Examples of those acid addition salts includehydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

[in the formula (II), Het1 represents a 3-pyridyl group,

R1 represents a hydroxyl group,

R2 and R3 represent a cyclopropylcarbonyloxy group, and

R4 represents a hydroxyl group]

More preferred examples of other insecticides which may be mixed withthe novel iminopyridine derivative represented by Formula (I) includeacetamiprid, imidacloprid, nitenpyram, clothianidin, acetamiprid,dinotefuran, thiacloprid, thiamethoxam, pymetrozine, spinosad,spinetram, fipronil, chloranthraniliprole, cyantraniliprole), cartap,thiocyclam, benfuracarb, buprofezin, ethofenprox, silafluofen,ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin,emamectin benzoate, cycloxaprid,1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate,afidopyropen, and the compound represented by Formula (II), oragriculturally and zootechnically acceptable acid addition saltsthereof, and particularly preferred examples thereof include permethrin,acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid,thiamethoxam, pymetrozine, spinosad, spinetram, fipronil,chloranthraniliprole, cyantraniliprole, amitraz, ethofenprox,silafluofen, ethiprole, flonicamid, sulfoxaflor, flupyradifurone,flometoquin, ivermectin, moxidectin, emamectin benzoate, cycloxaprid,1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate,and afidopyropen, or agriculturally and zootechnically acceptable acidaddition salts thereof.

The novel iminopyridine derivative represented by Formula (I) may beused together or in combination with a microbial pesticide such as a BTagent and an entomopathogenic viral agent.

Examples of the fungicide which may be mixed with the noveliminopyridine derivative represented by Formula (I) include, forexample, a strobilurin-based compound such as azoxystrobin,orysastrobin, kresoxym-methyl and trifloxystrobin, ananilinopyrimidine-based compound such as mepanipyrim, pyrimethanil andcyprodinil, an azole-based compound such as triadimefon, bitertanol,triflumizole, etaconazole, propic onazole, penconazole, flusilazole,myclobutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz andsimec onazole, a quinoxaline-based compound such as quinomethionate, adithiocarbamate-based compound such as maneb, zineb, mancozeb,polycarbamate and propineb, a phenyl carbamate-based compound such asdiethofencarb, an organochlorine compound such as chlorothalonil andquintozene, a benzimidazole-based compound such as benomyl,thiophanate-methyl and carbendazole, a phenyl amide-based compound suchas metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl and cyprofuram, asulfenic acid-based compound such as dichlofluanid, a copper-basedcompound such as copper hydroxide and copper oxyquinoline(oxine-copper), an isoxazole-based compound such as hydroxyisoxazole, anorganic phosphorus-based compound such as fosetyl-aluminium andtolclofos-methyl, an N-halogenothioalkyl-based compound such as captan,captafol and folpet, a dicarboximide-based compound such as procymidone,iprodione and vinchlozolin, a benzanilide-based compound such asthifluzamide, furametpyr, flutolanil and mepronil, a morpholine-basedcompound such as fenpropimorph and dimethomorph, an organic tin-basedcompound such as fenthin hydroxide and fenthin acetate, acyanopyrrole-based compound such as fludioxonil and fenpiclonil,9-membered cyclic dilactone compounds such as acibenzolar-S-methyl,isotianil, tiadinil, carpropamid, diclocymet, fenoxanil, tricyclazole,pyroquilon, ferimzone, fthalide, fluazinam, cymoxanil, triforine,pyrifenox, probenazole, fenarimol, fenpropidin, pencycuron, cyazofamid,iprovalicarb, tebufloquin, benthiavalicarb-isopropyl, tolprocarb,validamycin, Kasugamycin, Streptomycin and UK-2As, a compoundrepresented by the following Formula (III), which is described in JP-ANo. 2009-078991, a compound represented by the following Formula (IV),which is described in Republication No. WO08/066148, and a compoundrepresented by the following Formula (V), which is described inRepublication No. WO09/028280, or agriculturally and zootechnicallyacceptable acid addition salts thereof.

[in the formula (III), R1 and R2 represent a hydrogen atom or ahaloalkyl group having 1 to 6 carbon atoms and the like (however, atleast one of R1 and R2 represents a haloalkyl group having 1 to 6 carbonatoms), R3 represents a hydrogen atom and the like, A represents OR4,SR5, NR6R7 or NR8NR9R10, R4 represents an alkyl group having 8 to 12carbon atoms and the like, R5 represents an alkyl group having 1 to 12carbon atoms and the like, R6 and R7 represent a hydrogen atom or analkyl group having 8 to 12 carbon atoms, and R8, R9 and R10 represent ahydrogen atom or an alkyl group having 1 to 12 carbon atoms and thelike]

[in the formula (IV), R1 and R2 represent a C1 to C6 alkyl group, anaryl group, a heteroaryl group, or a aralkyl group,

R3 and R4 represent a hydrogen atom, a C1 to C6 alkyl group, a halogenatom, or a C1 to C6 alkoxy group,

X represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, aC2 to C6 alkenyl group, a C2 to C6 alkynyl group, an aryl group, aheteroaryl group, or a C1 to C6 alkoxy group,

Y represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, ora C1 to C 6 alkoxy group, and

n represents 0 to 4, and m represents 0 to 6]

[in the formula (V), R1 represents an alkyl group and the like, R2 andR3 each independently represent a hydrogen atom, a haloalkyl group andthe like (however, at least one of R2 and R3 is a haloalkyl group having1 to 6 carbon atoms), A represents —OR4, —SR5, —NR6R7 or —NR8NR9R10, R4represents an alkyl group having 3 to 12 carbon atoms, R5 represents analkyl group having 1 to 12 carbon atoms, R6 represents a hydrogen atom,R7 represents an alkyl group having 5 to 12 carbon atoms, and R8, R9 andR10 each represent an alkyl group having 3 to 12 carbon atoms and thelike, an alkyl group having 1 to 12 carbon atoms and the like, ahydrogen atom and the like, an alkyl group having 5 to 12 carbon atomsand the like, and an alkyl group having 1 to 12 carbon atoms,respectively.]

More preferred examples of other fungicides which may be mixed with thenovel iminopyridine derivative represented by Formula (I) includeazoxystrobin, orysastrobin, thifluzamide, furametpyr, fthalide,probenazole, acibenzolar-S-methyl, tiadinil, isotianil, carpropamid,diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin,simeconazole, validamycin, kasugamycin and pencycuron, and particularlypreferred examples thereof include probenazole and tebufloquin.

Preferred examples of other pest control agents which may be mixed withthe novel iminopyridine derivatives represented by Formula (I) alsoinclude herbicides such as lipid synthesis inhibitors, acetolactatesynthesis inhibitors, photosystem inhibitors, protoporphyrinogen IXoxidation inhibitors, bleacher herbicides, amino acid synthesisinhibitors, dihydropteroate synthetase inhibitors, cell divisioninhibitors, very-long-chain fatty acid synthesis inhibitors, cellulosebiosynthesis inhibitors, decoupling agents, auxin-like herbicides, auxintransport inhibitors, and the like. Specific examples here arealloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop,clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop,diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P,fluazifop-P-butyl, haloxyfop, haloxyfop-P-methyl, haloxyfop-P,haloxyfop-P-methyl ester, metamifop, pinoxaden, profoxydim,propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl,quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim,tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon,dimepiperate, ethyl dipropylthiocarbamat (EPIC), esprocarb,ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb,trichloroacetic acid (TCA), thiobencarb, tiocarbazil, triallate,vernolate, sulfonylureas (amidosulfuron, azimsulfuron, bensulfuron,bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methylsodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron,tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron,triflusulfuron-methyl, and tritosulfuron), imazamethabenz,imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, triazolopyrimidine herbicides (chloransulam,cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam,penoxsulam, pyrimisulfan, and pyroxsulam), bispyribac,bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac,pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, flucarbazone,flucarbazone-sodium, propoxycarbazon, propoxycarbazon-sodium,thiencarbazone, thiencarbazone-methyl, triazine herbicides(chlorotriazine, triazinones, triazindiones, methylthiotriazines, andpyridazinones (for example, ametryn, atrazine, chloridazone, cyanazine,desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn,propazine, simazin, simetryn, terbumeton, terbuthylazin, terbutryn, andtrietazin)), arylureas (for example, chlorobromuron, chlorotoluron,chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron,linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron,monolinuron, neburon, siduron, tebuthiuron, and thiadiazuron),phenylcarbamate esters (for example, desmedipham, karbutilat,phenmedipham, and phenmedipham-ethyl), nitrile herbicides (for example,bromofenoxim, bromoxynil and its salts and esters, and ioxynil and itssalts and esters), uracils (for example, bromacil, lenacil, andterbacil), bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor,propanil, inhibitors of the photosystem (such as diquat,diquat-dibromide, paraquat, paraquatdichloride, and paraquat dimethylsulfate), acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, ozadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin, beflubutamid, diflufenican, fluridone,flurochloridone, flurtamone, norflurazon, pyrazolate, picolinafen,aclonifen, amitrole, clomazone, flumeturon, glyphosate and its salts,bialaphos, bialaphos-sodium, glufosinate, glufosinate-P,glufosinate-ammonium, asulam, dinitroanilines (for example, benfluralin,butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin,pendimethalin, prodiamine, and trifluralin), phosphoramidate herbicides(for example, amiprophos, amiprophos-methyl, and butamifos), benzoicacid herbicides (for example, chlorthal and chlorthal-dimethyl),pyridines (for example, dithiopyr and thiazopyr), benzamides (forexample, propyzamide and tebutam), chloroacetamides (for example,acetochlor, alachlor, butachlor, dimethachlor, dimethenamid,dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamide,pretilachlor, propachlor, propisochlor, and thenylchlor),oxyacetanilides (for example, flufenacet and mefenacet), acetanilides(for example, diphenamide, naproanilide, and napropamide),tetrazolinones (for example, fentrazamide), anilofos, cafenstrole,fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, chlorthiamid,dichlobenil, flupoxam, isoxaben, dinoseb, dinoterb, 4,6-dinitro-o-cresol(DNOC) and its salts, 2,4-D and its salts and esters, 2,4-B and itssalts and esters, aminopyralid and its salts (for example,aminopyralid-tris(2-hydroxypropyl)ammonium) and esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichlorprop and its salts and esters, dichlorprop-P and its salts andesters, fluroxypyr and its salts and esters,2-methyl-4-chlorophenoxyacetic acid (MCPA) and its salts and esters,MCPA-thioethyl, 4-(2-methyl-4-chlorophenoxy)butyric acid (MCPB) and itssalts and esters, mecoprop and its salts and esters, mecoprop-P and itssalts and esters, picloram and its salts and esters, quinclorac,quinmerac, 2,3,6-trichlorobenzoic acid (TBA (2,3,6)) and its salts andesters, triclopyr and its salts and esters, aminocyclopyrachlor and itssalts and esters, diflufenzopyr and its salts, naptalam and its salts,bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin,cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-methyl sulfate,dimethipin, disodium methanearsonate (DSMA), dymron, endothal and itssalts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl,flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleichydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide,methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone,pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane, and6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS499223-49-3) and its salts and esters.

Control agents for animal parasitic pests which may be mixed with thenovel iminopyridine derivatives represented by Formula (I) can beexemplified by organophosphate ester compounds, carbamate-basedcompounds, nereistoxin derivatives, organochlorine compounds,pyrethroid-based compounds, benzoyl urea-based compounds, juvenilehormone-like compounds, molting hormone-like compounds,neonicotinoid-based compounds, sodium channel blockers for nerve cells,insecticidal macrocyclic lactones, γ-aminobutyric acid (GABA)antagonists, ryanodine receptor agonistic compounds, insecticidal ureas,and the like. More preferred specific examples include organophosphateesters such as dichlorvos, EPN, fenitrothion, fenamifos, prothiofos,profenofos, pyraclofos, chlorpyrifos-methyl, diazinon, trichlorfon,tetrachlorvinphos, bromofenofos, cythioate, and fenthion;carbamate-based compounds such as methomyl, thiodicarb, aldicarb,oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb,pirimicarb, carbofuran, and benfuracarb; nereistoxin derivatives such ascartap and thiocyclam; organochlorine compounds such as dicofol andtetradifon; pyrethroid-based compounds such as allethrin, d⋅d-Tallethrin, dl⋅d-T80 allethrin, pyrethrins, phenothrin, flumethrin,cyfluthrin, d⋅d-T80 prarethrin, phthalthrin, transfluthrin, resmethrin,cyphenothrin, pyrethrum extract, synepirin 222, synepirin 500,permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin,fenvalerate, fluvalinate, ethofenprox, and silafluofen; benzoylurea-based compounds such as diflubenzuron, teflubenzuron, flufenoxuron,chlorfluazuron, and lufenuron; juvenile hormone-like compounds such asmethoprene; molting hormone-like compounds such as chromafenozide; andother compounds such as amitraz, chlordimeform, fipronil, etoxazole,imidacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram,thiacloprid, dinotefuran, spirodiclofen, pyriproxyfen, indoxacarb,spinosad, spinetoram, avermectin, milbemycin, metaflumizone,pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor,flupyradifurone, ivermectin, selamectin, moxidectin, doramectin,eprinomectin, milbemycin oxim, diethylcarbamazine citrate, deet,metoxadiazon, cyromazine, triflumuron, star anise oil, triclabendazole,flubendazole, fenbendazole, antimony sodium gluconate, levamisolehydrochloride, bithionol, dichlorofen, phenothiazine, piperazine carbonbisulfide, piperazine phosphate, piperazine adipate, piperazine citrate,melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate,pyrantel, praziquantel, febantel, emodepside, derquantel, monopantel,emamectin benzoate, cycloxaprid, and a compound represented by thefollowing Formula (VI) or agriculturally and zootechnically acceptableacid addition salts thereof. Examples of those acid addition saltsinclude hydrochloride, nitrate, sulfate, phosphate, or acetate and thelike.

More preferred examples are flumethrin, permethrin, fipronyl, pyriprol,imidacloprid, thiamethoxam, acetamiprid, dinotefuran, amitraz,metaflumizon, pyriproxyfen, fenitrothion, lufenuron, ethoxazol,spinosad, spinetoram, emodepside, emamectin benzoate, ivermectin,selamectin, moxidectin, doramectin, eprinomectin, derquantel, andmonopantel.

Particularly preferred examples include amitraz and the like.

When the pest control composition is a pest control agent foragricultural and horticultural, particularly preferred examples for thepresent invention are pest control compositions in which the noveliminopyridine derivative represented by Formula (I) is at least onecompound selected fromN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound P212),N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide(compound 1-20), orN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide(compound 1-45), and the other pest control agent includes at least oneinsecticide or fungicide selected from acetamiprid, imidacloprid,clothianidin, dinotefuran, thiacloprid, fipronil, thiamethoxam,pymetrozine, flonicamid, spinosad, cyantraniliprole,chloranthraniliprole, ethofenprox, silafluofen, ethiprole, sulfoxaflor,flupyradifurone, flometoquin, emamectin benzoate, cycloxaprid,1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate,and afidopyropen, orysastrobin, thifluzamide, furametpyr, fthalide,probenazole, acibenzolar-S-methyl, tiadinil, isotianil, carpropamid,diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin,azoxystrobin, simeconazole, validamycin, thifluzamide, furametpyr, andpencycuron.

The pest control composition of the present invention may be preparedusing the novel iminopyridine derivative represented by Formula (I),other insecticides, fungicides, herbicides, or control agents for animalparasites, and an agriculturally and zootechnically acceptable carrier(solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant,and other preparation adjuvants).

(Specific Examples of Pesticide Preparations)

When the pest control composition of the present invention is a pestcontrol agent for agricultural and horticultural, the composition isusually mixed with an agriculturally and horticulturally acceptablecarrier (solid carrier, liquid carrier, gaseous carrier, surfactant,dispersant and other adjuvants for preparation to be provided in anyformulation form of emulsifiable concentrates, liquid formulations,suspensions, wettable powders, flowables, dust, granules, tablets, oils,aerosols, fumigants and the like.

Examples of the solid carrier include talc, bentonite, clay, kaolin,diatomaceous earth, vermiculite, white carbon, calcium carbonate and thelike.

Examples of the liquid carrier include alcohols such as methanol,n-hexanol and ethylene glycol, ketones such as acetone, methyl ethylketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane,kerosene and lamp oil, aromatic hydrocarbons such as toluene, xylene andmethyl naphthalene, ethers such as diethyl ether, dioxane andtetrahydrofuran, esters such as ethyl acetate, nitriles such asacetonitrile and isobutyl nitrile, acid amides such as dimethylformamideand dimethylacetamide, vegetable oils such as soybean oil and cottonseedoil, dimethyl sulfoxide, water and the like.

Further, examples of the gaseous carrier include LPG, air, nitrogen,carbonic acid gas, dimethyl ether and the like.

As the surfactant or dispersant for emulsification, dispersion,spreading and the like, it is possible to use, for example, alkylsulfateesters, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers,polyhydricalcohol esters, lignin sulfonates or the like.

In addition, as the adjuvant for improving the properties of thepreparation, it is possible to use, for example, carboxymethylcellulose,gum arabic, polyethylene glycol, calcium stearate or the like.

The aforementioned solid carriers, liquid carriers, gaseous carriers,surfactants, dispersants and adjuvants may be used either alone or incombination, if necessary.

The content of active ingredients in the preparation is not particularlylimited, but is usually in the range of 1 to 75% by weight for theemulsifiable concentrate, 0.3 to 25% by weight for the dust, 1 to 90% byweight for the wettable powder, and 0.5 to 10% by weight for thegranular formulation.

The novel iminopyridine derivatives represented by Formula (I), apreparation including the same and a mixed formulation of other pestcontrol agents with the same may be applied to pest insects, plants,plant propagation materials (for example, seeds, plant leaves and stems,roots, soil, water surface and materials for cultivation), rooms whichrequire disturbing the invasion of pests and the like. The applicationthereof may be performed before and after the invasion of pests.

A pest control agent including at least one of the novel iminopyridinederivatives represented by Formula (I) may also be applied togenetically-modified crops.

In a preferred aspect thereof, examples of a pest control compositionfurther including an agriculturally and horticulturally acceptablecarrier include:

(1) a wettable powder composition containing 0.1 to 80% by weight of thenovel iminopyridine derivative represented by Formula (I), 0.1 to 80% byweight of an insecticide as another pest control agent, 0.6 to 30% byweight of a wetting agent and a dispersant, and 20 to 95% by weight ofan extender,

(2) a water dispersible granule composition containing 0.1 to 80% byweight of the novel iminopyridine derivative represented by Formula (I),0.1 to 80% by weight of an insecticide as another pest control agent,0.6 to 30% by weight of a wetting agent, a dispersant and a binder, and20 to 95% by weight of an extender,

(3) a flowable composition containing 0.1 to 80% by weight of the noveliminopyridine derivative represented by Formula (I), 0.1 to 80% byweight of an insecticide as another pest control agent, 5 to 40% byweight of a dispersant, a thickener, an antifreeze, an antiseptic and anantifoaming agent, and 20 to 94% by weight of water,

(4) an emulsifiable concentrate composition containing 0.1 to 80% byweight of the novel iminopyridine derivative represented by Formula (I),0.1 to 80% by weight of an insecticide as another pest control agent, 1to 30% by weight of an emulsifier and an emulsion stabilizer, and 20 to97% by weight of an organic solvent,

(5) a dust composition containing 0.1 to 80% by weight of the noveliminopyridine derivative represented by Formula (I), 0.1 to 80% byweight of an insecticide as another pest control agent, and 70 to 99.8%by weight of an extender,

(6) a low drift dust composition containing 0.1 to 80% by weight of thenovel iminopyridine derivative represented by Formula (I), 0.1 to 80% byweight of an insecticide as another pest control agent, and 70 to 99.8%by weight of an extender,

(7) a microgranule fine composition containing 0.1 to 80% by weight ofthe novel iminopyridine derivative represented by Formula (I), 0.1 to80% by weight of an insecticide as another pest control agent, 0.2 to10% by weight of a solvent or binder, and 70 to 99.6% by weight of anextender,

(8) a granule composition containing 0.1 to 80% by weight of the noveliminopyridine derivative represented by Formula (I), 0.1 to 80% byweight of an insecticide as another pest control agent, 0.5 to 30% byweight of a granulation auxiliary (surfactant) and a binder, and 20 to98% by weight of an extender, and

(9) a microcapsule composition containing 0.1 to 80% by weight of thenovel iminopyridine derivative represented by Formula (I), 0.1 to 80% byweight of an insecticide as another pest control agent, 1 to 50% byweight of a covering agent, an emulsifier, a dispersant and anantiseptic, and 20 to 98% by weight of water. Preferably, examplesthereof include compositions of (2), (3), (6) and (8)

(Specific Examples of Formulations for Animals)

When the pest control agent of the present invention is a control agentfor animal parasitic pests, the agent is provided in the form of liquidformulations, emulsifiable concentrates, liquid drops, sprays, foampreparations, granules, fine granules, dust, capsules, pills, tablets,chewable formulations, injections, suppositories, creams, shampoos,rinses, resin agents, fumigants, poison baits and the like, and isparticularly preferably provided in the form of liquid formulations andliquid drops. These forms can be prepared using the followingpharmaceutically acceptable carriers.

The liquid formulation may also be blended with a typical adjuvant forpreparation, such as an emulsifier, a dispersant, a spreading agent, awetting agent, a suspending agent, a preservative and a propellant, andmay also be blended with a typical film former. As the surfactant foremulsification, dispersion, spreading and the like, it is possible touse, for example, soaps, polyoxyalkylene alkyl (aryl) ethers,polyoxyethylene alkyl aryl ethers, polyoxyethylene fatty acid ester,higher alcohols, alkyl aryl sulfonates and the like. Examples ofdispersants include casein, gelatin, polysaccharides, ligninderivatives, saccharides, synthetic water soluble polymers and the like.Examples of spreading⋅wetting agents include glycerin, polyethyleneglycol and the like. Examples of suspending agents include casein,gelatin, hydroxypropylcellulose, gum arabic and the like, and examplesof stabilizers include phenolic antioxidants (BHT, BHA and the like),amine antioxidants (diphenylamine and the like), organic sulfurantioxidants and the like. Examples of preservatives include methylp-oxybenzoate, ethyl p-oxybenzoate, propyl p-oxybenzoate, butylp-oxybenzoate and the like. The aforementioned carriers, surfactants,dispersants and adjuvants may be used either alone or in combination, ifnecessary. Furthermore, perfumes, synergists and the like may also beincorporated. The suitable content of the active ingredients in the pestcontrol agent of the present invention is usually 1 to 75% by weight forthe liquid formulation.

Examples of carriers used for the preparation of creams includenon-volatile hydrocarbons (liquid paraffin and the like), lanolinhydrogenated fats and oils, higher fatty acids, fatty acid esters,animal and vegetable oils, silicone oils, water and the like. Further,emulsifiers, humectants, antioxidants, perfumes, borax and ultravioletabsorbers may also be used either alone or in combination, if necessary.Examples of emulsifiers include fatty acid sorbitan, polyoxyethylenealkyl ethers, and fatty acid polyoxyethylene and the like. The suitablecontent of the active ingredients in the pest control agent of thepresent invention is usually 0.5 to 75% by weight for the cream.

The capsules, pills or tablets may be used such that the activeingredients in the composition of the present invention are mixed with acarrier such as starch, lactose or talc, a disintegrator and/or abinder, such as magnesium stearate is added thereto, and, if necessary,the mixture is tableted.

Carriers for the preparation of injections need to be prepared as anaseptic solution, but the solution may contain other substances, forexample, a salt or glucose enough to isotonicate the solution withblood. As available carriers, “injections need to be prepared as anaseptic solution. For injections, the solution may contain, for example,a salt or glucose enough to isotonicate the solution with blood.Examples of available carriers for the preparation of injections includeesters such as fatty acid derivatives of glyceride, benzyl benzoate,isopropyl myristate and propylene glycol, and organic solvents such asN-methylpyrrolidone and glycerol formal. The content of the activeingredients in the pest control agent of the present invention isusually 0.01 to 10% by weight for the injection.

Examples of carriers for the preparation of resin agents include vinylchloride polymers, polyurethane and the like. Plasticizers such asphthalic acid esters, adipic acid esters and stearic acid may be addedto these bases, if necessary. After the active ingredients are kneadedinto the base, the kneaded product may be molded by injection molding,extrusion molding, press molding and the like. In addition, the moldedproduct may also be properly subjected to processes such as molding orcutting to form an ear tag for animals or insecticidal collar foranimals.

Examples of carriers for toxic baits include bait substances andattraction substances (farina such as wheat flour and corn flour, starchsuch as corn starch and potato starch, saccharides such as granulatedsugar, malt sugar and honey, food flavors such as glycerin, onion flavorand milk flavor, animal powders such as pupal powder and fish powder,various pheromones and the like). The suitable content of the activeingredients in the pest control agent of the present invention isusually 0.0001 to 90% by weight for the toxic bait.

The pest control composition according to the present invention may beused such that a preparation form prepared by independently including atleast one of the novel iminopyridine derivative represented by Formula(I) as the active ingredient in the composition, or acid addition saltsthereof and at least one of other pest control agents alone isformulated and these ingredients when used are mixed on the spot.

Therefore, according to another aspect of the present invention, thereis provided a combined product prepared by including at least one of thenovel iminopyridine derivative represented by Formula (I) as the activeingredient or acid addition salts thereof and at least one of other pestcontrol agents.

According to another preferred aspect of the present invention, in thecombined product, the novel iminopyridine derivative represented byFormula (I) or acid addition salts thereof is provided as a firstcomposition prepared by including the same as active ingredients, andother pest control agents is provided as a second composition preparedby including the same as active ingredients. In this case, the firstcomposition and the second composition may be any formulation form whichuses appropriate carriers or adjuvants in combination thereof in thesame manner as in the case of the aforementioned pest controlcomposition. The combined product may be provided in the form of apharmaceutical set.

According to still another aspect of the present invention, there isprovided a method for protecting useful plants or animals from pests,including: simultaneously or independently (preferably, each ingredientsimultaneously) applying at least one of the novel iminopyridinederivative represented by Formula (I), enantiomers thereof, mixturesthereof or acid addition salts thereof as an active ingredient and atleast one of other pest control agents to a region to be treated.

In the method, “simultaneously” applying also includes mixing at leastone of the novel iminopyridine derivative represented by Formula (I) oracid addition salts thereof and at least one of other pest controlagents before being applied to a region to be treated, and applying themixture thereto. “Independently” applying includes, without mixing theseingredients in advance, applying the novel iminopyridine derivativerepresented by Formula (I) or acid addition salts thereof earlier thanthe other ingredients, or applying the novel iminopyridine derivativerepresented by Formula (I) or acid addition salts thereof later than theother ingredients.

According to still another preferred aspect of the present invention,

there is provided a method for protecting useful plants or animals frompests, including: applying

(1) a first composition prepared by including at least one of the noveliminopyridine derivative represented by Formula (I) or acid additionsalts thereof as an active ingredient, and

(2) a second composition prepared by including at least one of otherpest control agents as an active ingredient

to a region to be treated.

According to yet another aspect of the present invention, there isprovided a method for protecting useful plants from pests, including:applying the composition or combined product of the present invention asit is or diluted to pests, useful plants, seeds of useful plants, soil,cultivation carriers or animals as a target, and preferably to usefulplants, soil or animals.

According to still yet another aspect of the present invention, there isprovided a use of the composition or combined product of the presentinvention in order to protect useful plants or animals from pests.

Furthermore, preferred examples of the method for applying thecomposition or combined product of the present invention to pests,useful plants, seeds of useful plants, soil or cultivation carriers as atarget include spray treatment, water surface treatment, soil treatment(mixing, irrigation and the like), nursery box treatment, surfacetreatment (application, dust coating and covering) or fumigationtreatment (treatment in enclosed space, such as covering soil with apolyfilm after soil injection) and the like, and more preferred examplesinclude water surface treatment, soil treatment, nursery box treatmentor surface treatment.

The throughput in the case of application to plants by spray treatmentis 0.1 g to 10 kg per 10 areas of cultivated land and preferably 1 g to1 kg, as an amount of active ingredients of the composition of thepresent invention.

Further, examples of a method for treating seeds, roots, tubers, bulbsor rhizomes of plants include a dipping method, a dust coating method, asmearing method, a spraying method, a pelleting method, a coating methodand a fumigating method for the seed. The dipping method is a method inwhich seeds are dipped in a liquid chemical solution, and the dustcoating method is classified into a dry dust coating method in which agranular chemical is adhered onto dry seeds, and a wet dust coatingmethod in which a powdery chemical is adhered onto seeds which have beenslightly soaked in water. In addition, the smearing method is a methodin which a suspended chemical is applied on the surface of seeds withina mixer and the spraying method is a method in which a suspendedchemical is sprayed onto the surface of seeds. Furthermore, thepelleting method is a method in which a chemical is mixed with a fillerand treated when seeds are pelleted together with the filler to formpellets having certain size and shape, the coating method is a method inwhich a chemical-containing film is coated onto seeds, and thefumigating method is a method in which seeds are sterilized with achemical which has been gasified within a hermetically sealed container.

Examples of the preferred treatment method of the composition of thepresent invention include a dipping method, a dust coating method, asmearing method, a spraying method, a pelleting method and a coatingmethod.

Further, the composition of the present invention may also be used to,in addition to seeds, germinated plants which are transplanted aftergermination or after budding from soil, and embryo plants. These plantsmay be protected by the treatment of the whole or a part thereof bydipping before transplantation.

The throughput in the case of application to seeds of plants is notparticularly limited, but preferably 1 g to 10 kg and more preferably100 g to 1 kg per 100 kg of seeds, as an amount of active ingredients ofthe composition of the present invention.

In addition, the method for application of the composition of thepresent invention to soil is not particularly limited, but preferredapplication methods are as follows.

Examples of the method include a method in which granules including thecomposition of the present invention are applied into soil or on soil.Particularly preferred soil application methods include spraying, stripeapplication, groove application, and planting hole application.

Furthermore, application by irrigating soil with a solution prepared byemulsifying or dissolving the composition of the present invention inwater is also a preferred soil application method.

Besides these methods, examples of preferred soil application methodsinclude application into a nutrient solution in nutrient solutionculture systems such as solid medium culture, for example, hydroponicculture, sand culture, NFT (nutrient film technique), rock wool cultureand the like for the production of vegetables and flowering plants, orapplication into a nursery box for paddy rice seedling (mixing with bedsoil and the like). The compound of the present invention may be applieddirectly to artificial culture soil including vermiculite and a solidmedium including an artificial mat for growing seedling.

The throughput of the composition of the present invention into watersurface, a nursery box or soil is not particularly limited, but is 0.1 gto 10 kg of preferably active ingredients per 10 ares of cultivated landand preferably 1 g to 1 kg. Further, as the method for applying thecomposition or combined product of the present invention to an appliedorganism, it is possible to control pests by administering the pestcontrol composition of the present invention into the applied organismeither orally or by injection, wholly or partly administering thecomposition into the body surface of an applied animal, or mounting thepest control agent formulated into a resin preparation or sheetpreparation on the applied organism. In addition, it is also possible tocontrol pests by covering places in which the invasion, parasitism andmovement of pests are expected with the pest control composition of thepresent invention.

The pest control composition of the present invention may be used as itis, but may be diluted with water, liquid carriers, commerciallyavailable shampoos, rinses, baits, breed cage bottoms and the like andapplied in some cases. When the pest control composition of the presentinvention is diluted with a dilution liquid (water) such as anemulsifiable concentrate, a flowable and a wettable powder and used, theamount is not particularly limited, but, preferably, the composition isapplied by diluting the composition in water and spraying the mixturesuch that the concentration of active ingredients is 10 to 10,000 ppm.Furthermore, when the pest control composition of the present inventionis administered to a target organism, the administration amount thereofis not particularly limited, but when the composition is percutaneouslyapplied, the amount of the composition is preferably in a range from0.01 to 500 mg per 1 kg of the body weight of the target organism. Whenthe composition is orally administered, the amount of the composition isin a range from 0.01 to 100 mg per 1 kg of the body weight of the targetorganism. When a resin preparation is mounted on the target organism,the amount of the composition contained in the resin preparation ispreferably in a range from 0.01 to 50% by weight per weight of the resinpreparation.

EXAMPLES

Hereinafter, the present invention will be specifically described withreference to Examples, but the present invention is not limited to theExamples.

Synthetic Example P1:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound P212)

(1) 25 g (270 mmol) of 2-aminopyridine was dissolved in 200 ml ofanhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamine wasadded thereto, and the mixture was cooled to 0° C. 38 ml (57 g, 270mmol) of anhydrous trifluoroacetic acid was added dropwise thereto over15 minutes, and the resulting mixture was stirred at room temperaturefor 2 hours. After the reaction was completed, the reaction solution wasinjected into about 100 ml of iced water, and the mixture was stirredfor 10 minutes. The mixture was transferred to a separatory funnel toperform liquid separation, and the organic layer was washed twice with150 ml of water and twice with 150 ml of a 1% HCl aqueous solution,dried over anhydrous magnesium sulfate and concentrated under reducedpressure to obtain 36 g (yield 71%) of2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene) acetamide.

1H-NMR (CDCl3, δ, ppm): 7.20 (1H, ddd), 7.83 (1H, td), 8.20 (1H, d),8.35 (1H, d), 10.07 (1H, brs) 13C-NMR (CDCl3, δ, ppm): 115.3, 115.5 (q),121.6, 139.1, 147.9, 149.5, 155.3 (q)

MS: m/z=191 (M+H)

(2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in200 ml of anhydrous acetonitrile, 24 g (126 mmol) of2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by theabove-described method and 21 g (151 mmol) of potassium carbonate wereadded thereto, and the resulting mixture was heated and refluxed for 6hours, and then stirred at room temperature for 10 hours. After thereaction was completed, the reaction solution was filtered and theliquid was concentrated under reduced pressure. Diethyl ether was addedthereto for crystallization, and the crystals thus obtained werecollected and washed well with diethyl ether and water. The crystalsthus obtained were dried under reduced pressure at 60° C. for 1 hour toobtain the subject material. Amount obtained 26 g (yield 66%).

1H-NMR (CDCl3, δ, ppm): 5.57 (2H, s), 6.92 (1H, td), 7.31 (1H, d), 7.80(1H, td), 7.87 (1H, dd), 7.99 (1H, dd), 8.48 (2H, m)

13C-NMR (CDCl3, δ, ppm): 53.8, 115.5, 117.2 (q), 122.1, 124.7, 130.0,139.2, 140.0, 142.5, 149.7, 151.8, 158.9, 163.5 (q)

MS: m/z=316 (M+H)

(3) Powder X-Ray Crystal Analysis

In the powder X-ray diffraction, measurement was performed under thefollowing conditions.

Device name: RINT-2200 (Rigaku Corporation)

X-ray: Cu-Kα (40 kV, 20 mA)

Scanning range: 4 to 40°, sampling width: 0.02° and scanning rate:1°/min

The results are as follows.

Diffraction angle (20) 8.7°, 14.2°, 17.5°, 18.3°, 19.8°, 22.4°, 30.9°and 35.3°

(4) Differential Scanning Calorimetry (DSC)

In the differential scanning calorimetry, measurement was performedunder the following conditions.

Device name: DSC-60

Sample cell: aluminum

Temperature range: 50° C. to 250° C. (heating rate: 10° C./min)

As a result, the melting point was observed at 155° C. to 158° C.

Another method of Synthetic Example P1

3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was addedthereto, and the resulting mixture was stirred at 80° C. for 8 hours andat room temperature for 5 hours. After the reaction was completed, DMFwas distilled off under reduced pressure, acetonitrile was added theretoto precipitate a solid, and the solid was collected, washed well withacetonitrile and dried to obtain 2.07 g (yield 44%) of1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride.

1H-NMR (DMSO-d6, δ, ppm): 5.65 (2H, s), 6.96 (1H, t), 7.23 (1H, m), 7.57(1H, d), 7.80 (1H, m), 7.91 (1H, m), 8.28 (1H, m), 8.49 (1H, d), 9.13(2H, brs)

50 mg (0.20 mmol) of the1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochlorideobtained by the above-described method was dissolved in 5 ml ofanhydrous dichloromethane, 122 mg (1.00 mmol) of DMAP and 50 mg (0.24mmol) of anhydrous trifluoroacetic acid were added thereto in sequenceunder ice cold conditions, and the resulting mixture was stirred at roomtemperature for 1 hour. After the reaction was completed, the reactionsolution was diluted with dichloromethane, washed with 1% hydrochloricacid, and then dried over anhydrous magnesium sulfate. Dichloromethanewas distilled off under reduced pressure to obtain the subject material.Amount obtained 42 mg (yield 67%). NMR was the same as that of theabove-described method.

Synthetic Example P2:2,2-dibromo-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide(Compound P241)

200 mg (0.78 mmol) of the1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochlorideobtained by the method described in another method of Synthetic ExampleP1, 238 mg (1.95 mmol) of DMAP and 224 mg (1.17 mmol) of EDC-HCl weredissolved in 10 ml of anhydrous dichloromethane, 101 μl (202 mg, 1.17mmol) of dibromoacetic acid was added thereto, and the resulting mixturewas stirred at room temperature overnight. After the reaction wascompleted, the reaction solution was diluted with dichloromethane,washed once with water and twice with a 1% HCl aqueous solution, andthen dried over anhydrous magnesium sulfate and concentrated underreduced pressure to obtain the subject material. Amount obtained 50 mg(yield 15%)

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 5.99 (1H, s), 6.78 (1H, td), 7.33(1H, d), 7.69 (1H, td), 7.76 (1H, dd), 7.93 (1H, dd), 8.39 (1H, d), 8.50(1H, d)

13C-NMR (CDCl3, δ, ppm): 44.6, 53.1, 113.7, 121.9, 124.8, 130.1, 138.2,139.7, 141.2, 149.5, 152.0, 159.4, 172.2

MS: m/z=418 (M+H)

Synthetic Example P3:N-[1-((6-chloro-5-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound P227)

4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methyl pyridine was dissolvedin 80 ml of carbon tetrachloride, 7.37 g (41.4 mmol) ofN-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, andthe resulting mixture was heated and refluxed overnight. After thereaction was completed, the reaction solution was returned to roomtemperature, concentrated under reduced pressure and purified by silicagel column chromatography (hexane:ethyl acetate=19:1) to obtain 3.06 g(yield 51%) of 5-(bromomethyl)-2-chloro-3-fluoropyridine.

1H-NMR (CDCl3, δ, ppm): 4.45 (2H, s), 7.54 (1H, dd), 8.23 (1H, s)

50 mg (0.22 mmol) of the 5-(bromomethyl)-2-chloro-3-fluoropyridineobtained by the aforementioned method was dissolved in 5 ml of anhydrousacetonitrile, 42 mg (0.22 mmol) of2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide obtained by themethod described in (1) of Reference Example 1 and 36 mg (0.26 mmol) ofpotassium carbonate were added thereto in sequence, and the resultingmixture was heated and refluxed for 7 hours. After the reaction wascompleted, the reaction solution was returned to room temperature tofilter insoluble materials, and the filtrate was concentrated underreduced pressure. Diethyl ether was added thereto to precipitate asolid, and thus the solid was collected, washed with diethyl ether, andthen dried under reduced pressure in a desiccator to obtain the subjectmaterial. Amount obtained 29 mg (yield 40%).

1H-NMR (CDCl3, δ, ppm): 5.54 (2H, s), 6.89 (1H, td), 7.76 (1H, dd), 7.80(1H, td), 7.85 (1H, d), 8.29 (1H, d), 8.57 (1H, d)

MS: m/z=334 (M+H)

Synthetic Example P4:N-[1-((6-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound P229)

500 mg (4.50 mmol) of 2-fluoro-5-methyl pyridine was dissolved in 50 mlof carbon tetrachloride, 1.20 g (6.76 mmol) of N-bromosuccinimide and 20mg of benzoyl peroxide were added thereto, and the resulting mixture washeated and refluxed for 2.5 hours. After the reaction was completed, thereaction solution was returned to room temperature, and the solvent wasdistilled off under reduced pressure and purified by silica gel columnchromatography (hexane:ethyl acetate=19:1) to obtain 300 mg (yield 35%)of 5-bromomethyl-2-fluoropyridine.

57 mg (0.30 mmol) of the 5-bromomethyl-2-fluoropyridine obtained by theaforementioned method was dissolved in 10 ml of anhydrous acetonitrile,57 mg (0.30 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamidesynthesized by the method described in (1) of Synthetic Example P1 and69 mg (0.50 mmol) of potassium carbonate were added thereto in sequence,and the resulting mixture was heated and refluxed for 6 hours. After thereaction was completed, the reaction solution was returned to roomtemperature to filter insoluble materials, and the filtrate wasconcentrated under reduced pressure. The filtrate was purified by silicagel column chromatography (hexane:ethyl acetate=1:1→3:1) to obtain thesubject material. Amount obtained 21 mg (yield 23%).

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.89 (1H, td), 6.94 (1H, d), 7.79(1H, td), 7.87 (1H, d), 8.03 (1H, m), 8.31 (1H, s), 8.54 (1H, d)

MS: m/z=300 (M+H)

Synthetic Example P5:N-[1-((6-bromopyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound P231)

500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 ml ofcarbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mgof benzoyl peroxide were added thereto, and the resulting mixture washeated and refluxed for 19 hours. After the reaction was completed, thereaction solution was returned to room temperature, concentrated underreduced pressure and purified by silica gel column chromatography(hexane:ethyl acetate=19:1) to obtain 143 mg (yield 20%) of2-bromo-5-bromomethylpyridine.

1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 7.47 (1H, d), 7.59 (1H, dd), 8.38(1H, d)

70 mg (0.28 mmol) of the 2-bromo-5-bromomethylpyridine obtained by theaforementioned method was dissolved in 10 ml of anhydrous acetonitrile,54 mg (0.28 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamidesynthesized by the method described in (1) of Synthetic Example P1 and46 mg (0.34 mmol) of potassium carbonate were added thereto in sequence,and the resulting mixture was heated and refluxed for 6 hours. After thereaction was completed, the reaction solution was returned to roomtemperature to filter insoluble materials, and the filtrate wasconcentrated under reduced pressure. Diethyl ether was added thereto toprecipitate a solid, and thus the solid was collected, washed withdiethyl ether, and then dried under reduced pressure in a desiccator toobtain the subject material. Amount obtained 81 mg (yield 82%).

1H-NMR (CDCl3, δ, ppm): 5.52 (2H, s), 6.88 (1H, t), 7.48 (1H, d), 7.78(2H, m), 7.84 (1H, d), 8.44 (1H, d), 8.53 (1H, d)

MS: m/z=360 (M+H)

Synthetic Example P6:2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide(Compound P236)

70 mg (0.27 mmol) of the1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochlorideobtained by the method described in another method of Synthetic ExampleP1 was dissolved in 4 ml of anhydrous dichloromethane, 82 mg (0.67 mmol)of DMAP, 25 mg (0.27 mmol) of chloroacetic acid and 62 mg (0.32 mmol) ofEDC-HCl were added thereto in sequence, and the resulting mixture wasstirred at room temperature overnight. After the reaction was completed,dichloromethane was added thereto to dilute the mixture, and the mixturewas washed with water and a 1% HCl aqueous solution, dried overanhydrous magnesium sulfate and concentrated under reduced pressure toobtain the subject material. Amount obtained 4 mg (yield 5%).

1H-NMR (CDCl3, δ, ppm): 4.17 (2H, s), 5.46 (2H, s), 6.64 (1H, td), 7.31(1H, d), 7.60 (1H, td), 7.64 (1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.45(1H, d)

MS: m/z=296 (M+H)

Synthetic Example P7:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide(Compound P238)

400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml ofanhydrous dichloromethane, 322 μl (490 mg, 5.11 mmol) of difluoroaceticacid, 982 mg (5.10 mmol) of EDC-HCl and 622 mg (5.11 mmol) of DMAP wereadded thereto, and the resulting mixture was stirred at room temperaturefor 61 hours. After the reaction was completed, the reaction solutionwas diluted with dichloromethane, washed once with water and twice witha 1% HCl aqueous solution, and then dried over anhydrous magnesiumsulfate and concentrated under reduced pressure to obtain 102 mg (yield14%) of 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.

1H-NMR (CDCl3, δ, ppm): 6.03 (1H, t), 7.15 (1H, m), 7.78 (1H, td), 8.20(1H, d), 8.34 (1H, dd), 8.72 (1H, brs)

100 mg (0.58 mmol) of the2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by theaforementioned method was dissolved in 10 ml of anhydrous acetonitrile,94 mg (0.58 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 5ml of anhydrous acetonitrile and added thereto, and subsequently, 84 mg(0.63 mmol) of potassium carbonate was added thereto and the resultingmixture was heated and refluxed for 140 minutes. After the reaction wascompleted, the reaction solution was returned to room temperature tofilter off insoluble materials, and the filtrate was concentrated underreduced pressure. Ether was added thereto to precipitate a solid, andthus the solid was collected and dried well to obtain the subjectmaterial. Amount obtained 63 mg (yield 37%).

1H-NMR (CDCl3, δ, ppm): 5.52 (2H, s), 5.90 (1H, t), 6.79 (1H, td), 7.33(1H, d), 7.71 (1H, m), 7.77 (1H, dd), 7.85 (1H, dd), 8.45 (1H, d), 8.50(1H, d)

13C-NMR (DMSO-d6, δ, ppm): 53.0, 111.0 (t), 115.2, 120.7, 124.7, 131.7,140.6, 141.6, 143.2, 150.4, 150.9, 158.3, 169.4 (t)

MS: m/z=298 (M+H)

Synthetic Example P8:2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide(Compound P239)

200 mg (2.13 mmol) of 2-aminopyridine was dissolved in 5 ml ofdichloromethane, 491 mg (2.55 mmol) of EDC-HCl, 311 mg (2.55 mmol) ofDMAP and 187 μl (2.23 mmol, 290 mg) of chlorodifluoroacetic acid wereadded thereto in sequence, and the resulting mixture was stirredovernight. After the reaction was completed, the reaction solution wasdiluted with dichloromethane, washed with water and 1% hydrochloricacid, and then dried over anhydrous magnesium sulfate to obtain 105 mg(yield 24%) of 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.

1H-NMR (CDCl3, δ, ppm): 7.19 (1H, dd), 7.82 (1H, m), 8.18 (1H, d), 8.36(1H, d), 9.35 (1H, brs)

53 mg (0.33 mmol) of 2-chloro-5-chloromethyl pyridine dissolved in 6 mlof anhydrous acetonitrile was added to 68 mg (0.33 mmol) of the2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide synthesized bythe aforementioned method, and subsequently, 50 mg (0.36 mmol) ofpotassium carbonate was added thereto and the resulting mixture washeated and refluxed for 1 hours. After the reaction was completed, thereaction solution was returned to room temperature and then concentratedunder reduced pressure. Diethyl ether was added thereto to precipitate asolid, and thus the solid was collected and dried to obtain the subjectmaterial. Amount obtained 49 mg (yield 45%).

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.92 (1H, t), 7.33 (1H, d), 7.82(1H, m), 7.91 (1H, dd), 8.02 (1H, d), 8.45 (1H, d), 8.48 (1H, d)

13C-NMR (CDCl3, δ, ppm): 53.8, 115.2, 120.1 (t), 122.1, 124.8, 139.0,140.0, 142.3, 150.0, 151.9, 159.1, 159.1, 165.8 (t)

MS: m/z=332 (M+H)

Synthetic Example P9:2,2,2-trichloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide(Compound P235)

70 mg (0.27 mmol) of the1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochlorideobtained by the method described in another method of Synthetic ExampleP1 was dissolved in 4 ml of anhydrous dichloromethane, 94 μl (0.68 mmol,68 mg) of triethylamine and 33 μg (0.27 mmol, 49 mg) of trichloroacetylchloride were added thereto in sequence, and the resulting mixture wasstirred at room temperature for 1 hour. After the reaction wascompleted, water was added thereto to stop the reaction and liquidseparation was performed with dichloromethane and water. The organiclayer was washed once with water and twice with 1% hydrochloric acid,dried over anhydrous magnesium sulfate and concentrated under reducedpressure. Diethyl ether was added thereto to precipitate a solid, andthus the solid was collected and dried to obtain the subject material.Amount obtained 61 mg (yield 62%).

1H-NMR (CDCl3, δ, ppm): 5.59 (2H, s), 6.86 (1H, t), 7.32 (1H, d), 7.78(1H, td), 7.91 (2H, m), 8.43 (1H, d), 8.50 (1H, d)

MS: m/z=364 (M+H)

Synthetic Example P10:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,3,3,3-pentafluoropropanamide(Compound P242)

300 mg (3.19 mmol) of 2-aminopyridine was dissolved in 15 ml ofanhydrous dichloromethane, 919 mg (4.78 mmol) of EDC-HCl, 583 mg (4.78mmol) of DMAP and 397 μl (628 mg, 3.83 mmol) of pentafluoropropionicacid were added thereto in sequence, and the resulting mixture wasstirred at room temperature overnight. After the reaction was completed,the reaction solution was diluted with dichloromethane, washed once withwater and twice with 1% hydrochloric acid, and then dried over anhydrousmagnesium sulfate and concentrated under reduced pressure to obtain 85mg (yield 11%) of2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide.

52 mg (0.32 mmol) of 2-chloro-5-chloromethyl pyridine dissolved in 8 mlof anhydrous acetonitrile and 49 mg (0.35 mmol) of potassium carbonatewere added to 77 mg (0.32 mmol) of the2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide obtained bythe aforementioned method, and the resulting mixture was heated andrefluxed for 11 hours. After the reaction was completed, the reactionsolution was returned to room temperature to filter insoluble materials,and the filtrate was concentrated under reduced pressure. The filtratewas purified by silica gel column chromatography (hexane:ethylacetate=1:3) to obtain the subject material. Amount obtained 12 mg(yield 10%).

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.90 (1H, td), 7.32 (1H, d), 7.79(2H, m), 7.84 (1H, d), 8.43 (1H, d), 8.56 (1H, d)

MS: m/z=366 (M+H)

Synthetic Example P11:N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound P243)

1.04 g (8.13 mmol) of 2-chloro-5-methyl pyrimidine was dissolved in 30ml of carbon tetrachloride, 1.73 g (9.75 mmol) of N-bromosuccinimide and20 mg of benzoyl peroxide were added thereto, and the resulting mixturewas heated and refluxed for 6 hours. After the reaction was completed,the reaction solution was returned to room temperature, concentratedunder reduced pressure and purified by silica gel column chromatography(hexane:ethyl acetate=3:1) to obtain 641 mg (yield 38%) of5-bromomethyl-2-chloropyridine.

1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 8.66 (2H, s)

104 mg (0.50 mmol) of the 5-bromomethyl-2-chloropyridine obtained by theaforementioned method was dissolved in 6 ml of anhydrous acetonitrile,96 mg (0.50 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamideobtained by the method described in (1) of Synthetic Example P1 and 76mg (0.55 mmol) of potassium carbonate were added thereto, and theresulting mixture was heated and refluxed for 1 hour. After the reactionwas completed, the reaction solution was returned to room temperature tofilter off insoluble materials, and the filtrate was concentrated underreduced pressure. Diethyl ether was added thereto to precipitate asolid, and thus the solid was collected, washed with diethyl ether, andthen dried under reduced pressure in a desiccator to obtain the subjectmaterial. Amount obtained 92 mg (yield 58%).

1H-NMR (CDCl3, δ, ppm): 5.54 (2H, s), 6.98 (1H, m), 7.87 (1H, m), 8.18(1H, m), 8.48 (1H, m), 8.83 (2H, m)

13C-NMR (CDCl3, δ, ppm): 60.0, 115.6, 117.1 (q), 122.1, 127.5, 139.2,142.9, 158.8, 160.3 (2C), 161.4, 163.8 (q)

MS: m/z=317 (M+H)

The compounds of P213 to P226, P228, P230, P232 to P234, P240 and P244shown in the following Table were synthesized by the methods inaccordance with Synthetic Examples P1 to P11.

TABLE 40

Com- IR (KBr, pound ¹H-NMR (CDCl3, v, cm⁻¹) No. Ar R1a Y δ, ppm) or MSP212 6-chloro- CF3 H 5.57 (2H, s), 6.92 m/z = 3-pyridyl (1H, td), 7.31(1H, 316 d), 7.80 (1H, td), (M + H) 7.87 (1H, dd), 7.99 (1H, dd), 8.48(2H, m) P213 2-chloro- CF3 H 5.61 (2H, s), 6.93 m/z = 5- (1H, dd), 7.68(1H, s), 322 thiazolyl 7.83 (1H, td), 7.97 (M + H) (1H, d), 8.53 (1H, d)P214 6-chloro- OCH3 H 3.74 (3H, s), 5.40 m/z = 3-pyridyl (2H, s), 6.45(1H, 278 td), 7.29 (1H, d), (M + H) 7.46 (2H, m), 7.73 (1H, dd), 8.12(1H, dd), 8.40 (1H, d) P215 6-chloro- CF3 5- 5.53 (2H, s), 7.34 m/z =3-pyridyl Cl (1H, d), 7.71 (1H, 350 dd), 7.87 (1H, dd), (M + H) 7.94(1H, s), 8.49 (1H, d), 8.55 (1H, s) P216 6-chloro- CF3 5- 5.54 (2H, s),7.34 m/z = 3-pyridyl F (1H, d), 7.70 (1H, m), 334 7.80 (1H, m), 7.88(M + H) (1H, dd), 8.48 (1H, d), 8.64 (1H, m) P217 6-chloro- CF3 4- 5.49(2H, s), 6.85 m/z = 3-pyridyl Cl (1H, dd), 7.35 (1H, 350 d), 7.76 (1H,dd), (M + H) 7.85 (1H, dd), 8.44 (1H, d), 8.62 (1H, s) P218 2-chloro-CF3 5- 5.56 (2H, s), 7.68 m/z = 5- Cl (1H, s), 7.74 (1H, 356 thiazolyldd), 7.84 (1H, d), (M + H) 8.58 (1H, d) P219 2-chloro- CF3 5- 5.60 (2H,s), 7.69 m/z = 5- F (1H, s), 7.72 (1H, 340 thiazolyl td), 7.86 (1H, m),(M + H) 8.67 (1H, m) P220 2-chloro- CF3 4- 5.58 (2H, s), 6.90 m/z = 5-Cl (1H, d), 7.67 (1H, s), 356 thiazolyl 7.90 (1H, d), 8.61 (M + H) (1H,s) P221 6-chloro- CF3 3- 2.31 (3H, s), 5.50 m/z = 3-pyridyl Me (2H, s),6.98 (1H, m), 330 7.34 (1H, d), 7.73 (M + H) (1H, dd), 7.77 (2H, m),8.42 (1H, d) P222 6-chloro- CF3 4- 2.40 (3H, S), 5.49 m/z = 3-pyridyl Me(2H, s), 6.70 (1H, 330 dd), 7.32 (1H, d), (M + H) 7.70 (1H, d), 7.86(1H, dd), 8.37 (1H, s), 8.43 (1H, d) P223 6-chloro- CF3 5- 2.29 (3H, s),5.52 m/z = 3-pyridyl Me (2H, s), 7.32 (1H, d), 330 7.62 (1H, s), 7.65(M + H) (1H, dd), 7.88 (1H, dd), 8.46 (1H, d), 8.50 (1H, d) P224 phenylCF3 H 5.58 (2H, s), 6.81 m/z = (1H, m), 7.37 (4H, m), 281 7.77 (2H, m),8.50 (M + H) (1H, d) P225 4- CF3 H 5.52 (2H, s), 6.85 m/z = chlorophen-(1H, m), 7.30 (2H, d), 315 yl 7.36 (2H, d), 7.75 (M + H) (1H, td), 7.84(1H, d), 8.47 (1H, d) P226 3-pyridyl CF3 H 5.57 (2H, s), 6.86 m/z = (1H,m), 7.26-7.35 282 (2H, m), 7.78 (1H, (M + H) td), 7.86 (1H, m), 8.63(2H, m), 8.67 (1H, d) P227 6-chloro- CF3 H 5.54 (2H, s), 6.89 m/z =5-fluoro- (1H, td), 7.76 (1H, 334 3-pyridyl dd), 7.80 (1H, td), (M + H)7.85 (1H, d), 8.29 (1H, d), 8.57 (1H, d) P228 6- CF3 H 5.62 (2H, s),6.90 m/z = trifluro- (1H, t), 7.69 (1H, 350 methyl-3- d), 7.81 (1H, t),(M + H) pyridyl 7.88 (1H, d), 8.06 (1H, d), 8.56 (1H, d), 8.78 (1H, s)P229 6-fluoro- CF3 H 5.56 (2H, s), 6.89 m/z = 3-pyridyl (1H, td), 6.94(1H, 300 d), 7.79 (1H, td), (M + H) 7.87 (1H, d), 8.03 (1H, m), 8.31(1H, s), 8.54 (1H, d) P230 5,6- CF3 H 5.49 (2H, s), 6.89 m/z = dichloro-(1H, t), 7.79-7.90 350 3-pyridyl (2H, m), 8.04 (1H, (M + H) d), 8.37(1H, d), 8.56 (1H, m)

TABLE 41

IR Com- (KBr, pound ¹H-NMR (CDCl3, v, cm⁻¹) No. Ar R1a Y δ, ppm) or MSP231 6-bromo- CF3 H 5.52 (2H, s), 6.88 m/z = 3-pyridyl (1H, t), 7.48(1H, d), 360 7.78 (2H, m), 7.84 (M + H) (1H, d), 8.44 (1H, d), 8.53 (1H,d) P232 6-chloro- CF3 4- 5.52 (2H, s), 6.71 m/z = 3-pyridyl F (1H, m),7.35 (1H, d), 334 7.86 (1H, dd), 7.94 (M + H) (1H, m), 8.33 (1H, dd),8.44 (1H, d) P233 6-chloro- CF3 3- 5.53 (2H, s), 6.74 m/z = 3-pyridyl F(1H, m), 7.33 (1H, d), 334 7.87 (1H, dd), 8.07 (M + H) (1H, m), 8.29(1H, dd), 8.45 (1H, d) P234 6-chloro- CHCl2 H 5.54 (2H, s), 6.02 m/z =3-pyridyl (1H, s), 6.77 (1H, t), 330 7.32 (1H, m), 7.69 (M + H) (1H, m),7.77 (1H, d), 7.89 (1H, m), 8.42 (1H, m), 8.49 (1H, s) P235 6-chloro-CCl3 H 5.59 (2H, s), 6.86 m/z = 3-pyridyl (1H, t), 7.32 (1H, d), 3647.78 (1H, td), 7.91 (M + H) (2H, m), 8.43 (1H, d), 8.50 (1H, d) P2366-chloro- CH2Cl H 4.17 (2H, s), 5.46 m/z = 3-pyridyl (2H, s), 6.64 (1H,296 td), 7.31 (1H, d), (M + H) 7.60 (1H, td), 7.64 (1H, dd), 7.80 (1H,dd), 8.32 (1H, d), 8.45 (1H, d) P238 6-chloro- CHF2 H 5.52 (2H, s), 5.90m/z = 3-pyridyl (1H, t), 6.79 (1H, 298 td), 7.33 (1H, d), (M + H) 7.71(1H, m), 7.77 (1H, dd), 7.85 (1H, dd), 8.45 (1H, d), 8.50 (1H, d) P2396-chloro- CF2Cl H 5.56 (2H, s), 6.92 m/z = 3-pyridyl (1H, t), 7.33 (1H,d), 332 7.82 (1H, m), 7.91 (M + H) (1H, dd), 8.02 (1H, d), 8.45 (1H, d),8.48 (1H, d) P240 6-chloro- CH2ClBr H 5.53 (1H, d), 5.58 m/z = 3-pyridyl(1H, d), 6.06 (1H, s), 374 6.76 (1H, td), 7.32 (M + H) (1H, d), 7.69(1H, m), 7.70 (1H, m), 7.90 (1H, dd), 8.40 (1H, d), 8.50 (1H, d) P2416-chloro- CHBr2 H 5.56 (2H, s), 5.99 m/z = 3-pyridyl (1H, s), 6.78 (1H,418 td), 7.33 (1H, d), (M + H) 7.69 (1H, td), 7.76 (1H, dd), 7.93 (1H,dd), 8.39 (1H, d), 8.50 (1H, d) P242 6-chloro- CF2CF3 H 5.56 (2H, s),6.90 m/z = 3-pyridyl (1H, td), 7.32 (1H, 366 d), 7.79 (2H, m), 7.84 (M +H) (1H, d), 8.43 (1H, d), 8.56 (1H, d) P243 2-chloro- CF3 H 5.54 (2H,s), 6.98 m/z = 5- (1H, m), 7.87 (1H, m), 317 pyrimi- 8.18 (1H, m), 8.48(M + H) dinyl (1H, m), 8.83 (2H, m) P244 6-chloro- CH2Br H 4.17 (2H, s),5.46 3-pyridyl (2H, s), 6.63 (1H, td), 7.31 (1H, d), 7.60 (1H, td), 7.65(1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.47 (1H, d)

Synthetic Example 1:2,2-difluoro-N-[1-((6-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]acetamide(Compound 3-3)

(1) 400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml ofanhydrous dichloromethane, 322 μl (490 mg, 5.11 mmol) of difluoroaceticacid, 982 mg (5.10 mmol) of EDC-HCl and 622 mg (5.11 mmol) of DMAP wereadded thereto, and the resulting mixture was stirred at room temperaturefor 61 hours. After the reaction was completed, the reaction solutionwas diluted with dichloromethane, washed once with water and twice witha 1% HCl aqueous solution, and then dried over anhydrous magnesiumsulfate and concentrated under reduced pressure to obtain 102 mg (yield14%) of 2,2-difluoro-N-(pyridin-2(1H)-ylidene) acetamide.

1H-NMR (CDCl3, δ, ppm): 6.03 (1H, t), 7.15 (1H, m), 7.78 (1H, td), 8.20(1H, d), 8.34 (1H, dd), 8.72 (1H, brs)

(2) 128 mg (0.75 mmol) of 5-bromomethyl-2-fluoropyridine was dissolvedin 3 ml of anhydrous DMF, 116 mg (0.68 mmol) of2,2-difluoro-N-[pyridin-2(1H)-ylidene]acetamide was dissolved in 3 ml ofanhydrous DMF and added thereto, and subsequently, 103 mg (0.75 mmol) ofpotassium carbonate was added thereto and the resulting mixture wasstirred at 65° C. for 2 hours. After the reaction was completed, thereaction solution was returned to room temperature, and ethyl acetateand water were added thereto to perform liquid separation. The organiclayer was washed with 1% hydrochloric acid, then dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. A smallamount of hexane and diethyl ether were added thereto to precipitatecrystals, and thus the crystals were collected and dried to obtain thesubject material. Amount obtained 50 mg (yield 26%).

Synthetic Example 2:N-[1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(Compound 190-2)

(1) 300 mg (1.86 mmol) of 2-chloro-5-chloromethyl pyridine was dissolvedin 6 ml of anhydrous DMF, 118 mg (1.24 mmol) of 2-aminopyrimidine wasadded thereto, and the resulting mixture was stirred at 80° C. for 8hours. After the reaction was completed, the reaction solution wasreturned to room temperature to distill off DMF under reduced pressure.Diethyl ether was added thereto, and thus crystallization was occurredon the wall surface of an eggplant flask. Diethyl ether was removed bydecantation and dried well to obtain1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-imine hydrochloride.Amount obtained 107 mg (yield 34%)

(2) 71 mg (0.27 mmol) of the1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-imine hydrochlorideobtained by the aforementioned method was suspended in 5 ml of anhydrousdichloromethane, 114 μl (0.83 mmol, 83 mg) of triethylamine and 53 μl(0.38 mmol) of trifluoroacetic anhydride were added thereto in sequence,and the resulting mixture was stirred at room temperature for 2 hours.After the reaction was completed, dichloromethane and water were addedto the reaction solution to perform liquid separation, and the organiclayer was dried over anhydrous magnesium sulfate and then concentratedunder reduced pressure. A small amount of diethyl ether was addedthereto to precipitate crystals, and thus the crystals were collected,washed with a small amount of diethyl ether, and then dried to obtainthe subject material. Amount obtained 24 mg (yield 28%).

Synthetic Example 3:2,2,2-trifluoroethyl-[1-((6-chloropyridin-3-yl)methyl)pyridin-(2H)-ylidene]carbamate(Compound 1-17)

(1) 3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissolvedin 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine wasadded thereto, and the resulting mixture was stirred at 80° C. for 8hours and at room temperature for 5 hours. After the reaction wascompleted, DMF was distilled off under reduced pressure, acetonitrilewas added thereto to precipitate a solid, and the solid was collected,washed well with acetonitrile and then dried to obtain 2.07 g (yield44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-iminehydrochloride.

1H-NMR (DMSO-d6, δ, ppm): 5.65 (2H, s), 6.96 (1H, t), 7.23 (1H, m), 7.57(1H, d), 7.80 (1H, m), 7.91 (1H, m), 8.28 (1H, m), 8.49 (1H, d)

(2) 10 ml of anhydrous acetonitrile was added to 150 mg (0.66 mmol) ofthe 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochlorideobtained by the aforementioned method, 177 mg (0.66 mmol) of4-nitrophenyl (2,2,2-trifluoroethyl)carbamate and 200 mg (1.46 mmol) ofpotassium carbonate were added, and the resulting mixture was stirred at50° C. for 2 hours. After the reaction was completed, the reactionsolution was returned to room temperature to filter off insolublematerials, and the filtrate was concentrated under reduced pressure.Dichloromethane and water were added thereto to perform liquidseparation, and the organic layer was washed with 1% hydrochloric acid,then dried over anhydrous magnesium sulfate and concentrated underreduced pressure. A small amount of diethyl ether was added thereto toprecipitate crystals, and thus the crystals were collected and driedwell to obtain the subject material. Amount obtained 48 mg (yield 21%).

Synthetic Example 4:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide(Compound 1-20)

(1) 25 g (270 mmol) of 2-aminopyridine was dissolved in 200 ml ofanhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamine wasadded thereto, and the mixture was cooled to 0° C. 38 ml (57 g, 270mmol) of anhydrous trifluoroacetic acid was added dropwise thereto over15 minutes, and the resulting mixture was stirred at room temperaturefor 2 hours. After the reaction was completed, the reaction solution wasinjected into about 100 ml of iced water, and the mixture was stirredfor 10 minutes. The mixture was transferred to a separatory funnel toperform liquid separation, and the organic layer was washed twice with150 ml of water and twice with 150 ml of a 1% HCl aqueous solution,dried over anhydrous magnesium sulfate and concentrated under reducedpressure to obtain 36 g (yield 71%) of2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene) acetamide.

1H-NMR (CDCl3, δ, ppm): 7.20 (1H, m), 7.83 (1H, m), 8.20 (1H, d), 8.35(1H, d), 10.07 (1H, brs)

13C-NMR (CDCl3, δ, ppm): 115.3, 115.5 (q), 121.6, 139.1, 147.9, 149.5,155.3 (q)

(2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in200 ml of anhydrous acetonitrile, 24 g (126 mmol) of2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by theabove-described method and 21 g (151 mmol) of potassium carbonate wereadded thereto, and the resulting mixture was heated and refluxed for 6hours, and then stirred at room temperature for 10 hours. After thereaction was completed, the reaction solution was filtered and thefiltrate was concentrated under reduced pressure. Diethyl ether wasadded thereto for crystallization, and the crystals thus obtained werecollected and washed well with diethyl ether and water. The crystalsthus obtained were dried under reduced pressure at 60° C. for 1 hour toobtainN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(P212). Amount obtained 26 g (yield 66%).

1H-NMR (CDCl3, δ, ppm): 5.57 (2H, s), 6.92 (1H, td), 7.31 (1H, d), 7.80(1H, td), 7.87 (1H, dd), 7.99 (1H, dd), 8.48 (2H, m)

13C-NMR (CDCl3, δ, ppm): 53.8, 115.5, 117.2 (q), 122.1, 124.7, 130.0,139.2, 140.0, 142.5, 149.7, 151.8, 158.9, 163.5 (q)

MS: m/z=316 (M+H)

(3) 180 ml of toluene was added to 16.3 g (36.7 mmol) of phosphoruspentasulfide, 6.72 g (63.4 mmol) of sodium carbonate was added theretoand the resulting mixture was stirred at room temperature for 5 minutes.20.0 g (63.4 mmol) of theN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamideobtained by the above-described method was added thereto, and theresulting mixture was stirred at 50° C. for 19 hours. 150 ml of ethylacetate was added to the reaction solution, the resulting mixture wasstirred at 50° C. for 10 minutes, then insoluble materials were filteredoff, and 250 ml of ethyl acetate was used to wash the mixture. Themixture was transferred to a separatory funnel, washed therein with 300ml of a saturated sodium bicarbonate water and 200 ml of a saturatedsaline solution, and then concentrated under reduced pressure. 200 ml ofwater was added thereto to precipitate crystals. The mixture was stirredat room temperature for 1 hour, and then the crystals were collected,subjected to slurry washing twice with 150 ml of water and twice with150 ml of hexane, and dried at 60° C. under reduced pressure for 2 hoursto obtain the subject material. Amount obtained 19.5 g (yield 94%).

1H-NMR (CDCl3, δ, ppm): 5.48 (2H, s), 7.12 (1H, td), 7.34 (1H, d), 7.77(1H, dd), 7.96 (1H, m), 8.05 (1H, dd), 8.45 (1H, d), 8.56 (1H, d)

MS: m/z=332 (M+H)

Synthetic Example 5:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-methylacetimidamide(Compound 1-42)

150 mg (0.45 mmol) of theN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide(1-20) synthesized by the method in Synthetic Example 4 was dissolved in5 ml of methanol, 105 μl (42 mg, 1.36 mmol) of methylamine (40% methanolsolution) and 124 mg (0.45 mmol) of silver carbonate were added thereto,and the resulting mixture was stirred at 50° C. for 1 hour. After thereaction was completed, the reaction solution was returned to roomtemperature and subjected to suction filtration by using celite toremove insoluble materials. Ethyl acetate and water were added theretoto perform liquid separation, and the organic layer was dried overanhydrous magnesium sulfate, then concentrated under reduced pressureand purified with silica gel column chromatography (hexane:ethylacetate=1:1) to obtain the subject material. Amount obtained 81 mg(yield 56%).

Synthetic Example 6:N′-(aryloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetimidamide(Compound 1-507)

30 mg (0.09 mmol) of theN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide(1-20) synthesized by the method in Synthetic Example 4 was dissolved in5 ml of ethanol, 50 mg (0.45 mmol) of 0-ally hydroxylaminehydrochloride, 62 μl (0.45 mmol, 45 mg) of triethylamine and 25 mg (0.09mmol) of silver carbonate were added thereto, and the resulting mixturewas stirred at 50° C. for 5 hours and 20 minutes. After the reaction wascompleted, the reaction solution was returned to room temperature tofilter off insoluble materials. The filtrate was concentrated underreduced pressure to perform liquid separation with ethyl acetate and 1%hydrochloric acid, then the ethyl acetate layer was washed with asaturated saline solution, and dried over anhydrous magnesium sulfateand then concentrated under reduced pressure. The ethyl acetate layerwas purified by a TLC plate (one sheet of 0.5 mm plate, evolved withhexane:ethyl acetate=1:1) to obtain the subject material. Amountobtained 15 mg (yield 45%).

Synthetic Example 7:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide(Compound 1-499)

25 ml of ethanol was added to 1.00 g (3.00 mmol) of theN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide(1-20) 1 synthesized by the method in Synthetic Example 4, 1.04 g (15.0mmol) of hydroxylamine hydrochloride and 2.00 ml (1.50 g, 15.0 mmol) oftriethylamine were added thereto in sequence, and the resulting mixturewas stirred at 50° C. for 21.5 hours. After the reaction was completed,ethyl acetate and 1% hydrochloric acid were added to the reactionsolution to perform liquid separation, and the organic layer was washedwith water, dried over anhydrous magnesium sulfate and concentratedunder reduced pressure. The organic layer was purified by silica gelcolumn chromatography (hexane:ethyl acetate=1:1) to obtain the subjectmaterial. Amount obtained 625 mg (yield 63%).

Synthetic Example 8:N-(benzoyloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetimidamide(Compound 1-519)

30 mg (0.09 mmol) of theN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide(1-499) synthesized by the method in Synthetic Example 7 was dissolvedin 3 ml of anhydrous acetonitrile, 24 μl (17 mg, 0.17 mmol) oftriethylamine and 20 μg (22 mg, 0.17 mmol) of benzoyl chloride wereadded thereto in sequence, and the resulting mixture was stirred at roomtemperature for 10 minutes. After the reaction was completed, ethylacetate and 1% hydrochloric acid were added to the reaction solution toperform liquid separation, and the organic layer was washed with water,dried over anhydrous magnesium sulfate and concentrated under reducedpressure. The organic layer was purified by a TLC plate (one sheet of0.5 mm plate, evolved with hexane:ethyl acetate=1:1) to obtain thesubject material. Amount obtained 26 mg (yield 67%).

Synthetic Example 9:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-((propylcarbamoyl)oxy)acetimidamide(Compound 1-534)

5 ml of anhydrous acetonitrile was added to 11 mg (0.13 mmol) of normalpropyl isocyanate, 40 mg (0.12 mmol) of theN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide(1-499) synthesized by the method in Synthetic Example 7 and 4 mg (0.04mmol) of potassium-t-butoxide were added thereto, and the resultingmixture was stirred at room temperature for 1 hour. After the reactionwas completed, the reaction solution was concentrated under reducedpressure, and ethyl acetate and a saturated saline solution were addedthereto to perform liquid separation. The ethyl acetate layer was driedover anhydrous magnesium sulfate, concentrated under reduced pressureand purified by a TLC plate (one sheet of 0.5 mm plate, evolved withhexane:ethyl acetate=1:3) to obtain the subject material. Amountobtained 16 mg (yield 32%).

Synthetic Example 10: Diisopropyl1-((6-chloropyridin-3-yl)methyl)pyridyn-2(1H)-ylidenphospholamidetrithioate (Compound 1-702)

4.0g (15.7 mmol) of 1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-iminehydrochloride obtained by the above-described method was suspended in24.6 ml of dichloromethane, and under ice-cooling 1.35 ml of phosphorpustrichloride over 10 mins, following 3.16g (31.2 mmol) of triethylaminedissolved in 37 ml of dichloromethane was added thereto. After themixture was stirred for 2 hours at room temperature, 499 mg (15.6 mmol)of sulfur was added to the mixture, and the mixture was stirred overnight at room temperature. Under ice-cooling 3.16g (31.2 mmol) oftriethylamine, following 2.38g (31.2 mmol) of 2-propanethiol dissolvedin 10 ml of dichloromethane were added to the mixture, additionary themixture was stirred for a day. After the reaction was completed, thereaction solution was concentrated under reduced pressure, and wasextracted by 100 ml of diethylether twice. The ether solution wasconcentrated under reduced pressure, and 2.49g of cruede compounds wasobtained. 186 mg of crude compound was purified by a TLC plate (5 sheetsof 0.5 mm plate, evolved with ethyl acetate) to obtain the subjectmaterial (47 mg. yield 9%) and(1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene)phosphoramidothioicdichloride (19 mg. yield 5%).

(1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene)phosphoramidothioic Dichloride Synthetic Example 11:N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-1,1,1-trifluoromethanesulfinamide(Compound1-703)

330 mg (2 mmol) of sodium trifluoromethanesulfonate was added by 2 ml ofethylacetate and 154 mg (1 mmol) of phosphorus oxychloride and stirredfor 5 min at room temperature. And 220 mg (0.86 mmol) of1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-imine hydrochlorideobtained by the above-described method was added to the mixture, andstirred for 2 hours. After the reaction was completed, the reactionmixture was purified by silica-gel column chromatography (eluentethylacetate:hexane=1:1) to obtain the subject material (115 mg. yield39%)

The compounds shown in the following Table were prepared by the methodin accordance with Synthetic Examples 1 to 11.

TABLE 42 Com- Reaction pound Base and the temperature, Method Yield No.Raw material 1 Raw material 2 like Solvent Time (Table) (%) 266-2 69 mg(0.43 mmol) of 84 mg (0.43 mmol) 71 mg (0.52 mmol) Acetonitrile reflux,20 h A 32 2-chloro-5- of 2,2,2- of (chloromethyl)pyridine trifluoro-N-potassium (1,3,4- carbonate thiadiazol- 2(3H)- ylidene))acetamide 444-256 mg (0.41 mmol) of 66 mg (0.34 mmol) 56 mg (0.41 mmol) Acetonitrilereflux, 20 h A 21 2-chloro-5- of 2,2,2- of (chloromethyl)thiazoletrifluoro-N- potassium (1,3,4- carbonate thiadiazol- 2(3H)-ylidene))acetamide 190-2 71 mg (0.27 mmol) of 53 μl (0.38 mmol) 53 μl(0.38 mmol) Dichloromethane Room B 28 1-((6-chloropyridin- of oftemperature, 3- anhydrous triethylamine 1 h yl)methyl)pyrimidin-trifluoroacetic 2(1H)-imine acid hydrochloride 201-2 120 mg (0.47 mmol)of 99 μl (0.71 mmol) 160 μl (1.17 mmol) Dichloromethane Room B 111-((6-chloropyridin- of of temperature, 3-yl)methyl)pyrazin- anhydroustriethylamine 30 min 2(1H)-imine trifluoroacetic hydrochloride acid223-2 530 mg (2.07 mmol) of 2- 390 μl (2.79 mmol) 537 μl (2.79 mmol)Dichloromethane Room B 14 chloro-2-((6- of anhydrous of temperature,chloropyridin-3- trifluoroacetic acid triethylamine 2 hyl)methyl)pyridazin- 3(2H)-imine hydrochloride 146-2 113 mg (0.70 mmol)of 2- 145 mg (0.70 mmol) 116 mg (0.84 mmol) Acetonitrile reflux, 13 h A15 chloro-5- of 2,2,2-trifluoro- of (chloromethyl)pyridineN-(3-hydroxypyridin- potassium 2(1H)- carbonate ylidene))acetamide 224-2190 mg (0.73 mmol) of 2- 168 μl (1.20 mmol) 220 μl (1.60 mmol)Dichloromethane Room B 16 ((2-chlorothiazol-5- of anhydrous oftemperature, yl)methyl)pyridazin- trifluoroacetic acid triethylamine 5min 3(2H)-imine hydrochloride 102-2 116 mg (0.72 mmol) of 2- 155 mg(0.72 mmol) 109 mg (0.79 mmol) Acetonitrile reflux, 8 h A 22 chloro-5-of N-(3- of (chloromethyl)pyridine cyanopyridin-2(1H)- potassiumylidene))2,2,2- carbonate trifluoroacetamide 212-2 59 mg (0.37 mmol) of2- 70 mg (0.37 mmol) of 55 mg (0.40 mmol) Acetonitrile reflux, 7 h A 32chloro-5- 2,2,2-trifluoro-N- of (chloromethyl)pyridine (pyrimidin-4(3H)-potassium ylidene))acetamide carbonate   1-20 20.0 g (63.4 mmol) ofN-[1- 16.3 g (36.7 mmol) of 6.72 mg Toluene 50° C., D 94((6-chloropyridin-3- phosphorus pentasulfide (63.4 mmol) 19 hyl)methyl)pyridin-2(1H)- of sodium ylidene]-2,2,2- carbonatetrifluoroacetamide  12-2 78 mg (0.38 mmol) of 2- 73 mg (0.38 mmol) of2,2,2- 58 mg (0.42 mmol) Acetonitrite reflux, A 44 chloro-4-trifluoro-N-(pyridin-2(1H)- of 3.5 h (bromomethyl)pyridineylidene))acetamide potassium carbonate 213-2 79 mg (0.47 mmol) of 2- 90mg (0.47 mmol) of 2,2,2- 72 mg (0.52 mmol) Acetonitrile reflux, A 42chloro-5- trifluoro-N-(pyrimidin- of 12 h (chloromethyl)thiazole4(3H)-ylidene))acetamide potassium carbonate   1-17 150 mg (0.66 mmol)of 1-[(6- 177 mg (0.66 mmol) of 4- 200 mg Acetonitrile 50° C., C 21chloropyridin-3- nitrophenyl(2,2,2- (1.46 mmol) 2 hyl)methyl]pyridin-2(1H)- trifluoroethyl)carbamate of imine hydrochloridepotassium carbonate   1-18 150 mg (0.66 mmol) of 1-[(6- 184 mg (0.66mmol) of 4- 200 mg Acetonitrile 50° C., C 30 chloropyridin-3-nitrophenyl(1,1,1- (1.46 mmol) 2 h yl)methyl]pyridin-2(1H)-trifluoropropan-2- of imine hydrochloride yl)carbamate potassiumcarbonate   1-19 150 mg (0.66 mmol) of 220 mg (0.66 mmol) of 200 mg(1.46 mmol) Acetonitrile 50° C., 3 h C 27 1-[(6-chloropyridin-3-1,1,1,3,3,3- of potassium yl)methyl]pyridin- hexafluoropropan-2-carbonate 2(1H)-imine yl(4- hydrochloride nitrophenyl)carbamate  7-2 116mg (0.72 mmol) of 137 mg (0.72 mmol) of 110 mg (0.80 mmol) Acetonitrilereflux, 5 h A 49 2-chloro-5- 2,2,2-trifluoro-N- of potassium(chloromethyl)pyrazine (pyridin-2(1H)- carbonate ylidene))acetamide  1-13 200 mg (0.78 mmol) of 103 μl (1.17 mmol) of EDC- DichloromethaneRoom B 21 1-[(6-chloropyridin-3- 2,2,2- HCl 225 mg(1.17 mmol),temperature, yl)methyl]pyridin- trifluoropropionic DMAP 238 mg 12 h2(1H)-imine acid (1.95 mmol) hydrochloride

TABLE 43 Reaction Compound Base and temperature, Method Yield No. Rawmaterial 1 Raw material 2 the like Solvent Time (Table) (%) 168-2  273mg (1.70 mmol) of 2- 350 mg (1.70 mmol) 248 mg DMF 65° C., 2 h A 15chloro-5- of 2,2,2-trifluoro- (1.80 mmol) (chloromethyl)pyridine N-(5-of hydroxypyridin- potassium 2(1H)- carbonate ylidene))acetamide  1-2123 mg (0.077 mmol) of N- 41 mg (0.092 mmol) 10 mg THF Room D 49[1-((6-chloropyridin-3- of phosphorus (0.092 mmol) temperature,yl)methyl)pyridin-2(1H)- pentasulfide of 2 h ylidene]-2,2- sodiumdifluoroacetamide carbonate  3-20 30 mg (0.10 mmol) of N- 49 mg (0.11mmol) 12 mg THF Room D 49 [1-((6-fluoropyridin-3- of phosphorus (0.11mmol) temperature, yl)methyl)pyridin-2(1H)- pentasulfide of 3 hylidene]-2,2,2- sodium trifluoroacetamide carbonate  4-20 30 mg (0.083mmol) of N- 41 mg (0.09 mmol) 10 mg THF Room D 61 [1-((6-bromopyridin-3-of phosphorus (0.09 mmol) temperature, yl)methyl)pyridin-2(1H)-pentasulfide of 3 h ylidene]-2,2,2- sodium trifluoroacetamide carbonate3-3 116 mg (0.72 mmol) of 2- 116 mg (0.68 mmol) 110 mg Acetonitrilereflux, A 27 fluoro-5- of 2,2-difluoro-N- (0.80 mmol) 6 h(bromomethyl)pyridine (pyridin-2(1H)- of ylidene))acetamide potassiumcarbonate 4-3 50 mg (0.20 mmol) of 2- 35 mg (0.20 mmol) of 33 mgAcetonitrile reflux, A 53 bromo-5- 2,2-difluoro-N- (0.24 mmol) 6 h(bromomethyl)pyridine (pyridin-2(1H)- of ylidene))acetamide potassiumcarbonate 5-5 46 mg (0.21 mmol) of 5- 50 mg (0.21 mmol) of 35 mgAcetonitrile reflux, A 26 (bromomethyl)-2-chloro- 2,2,3,3,3- (0.25 mmol)2 h 3-fluoropyridine pentafluoro-N- of (pyridin-2(1H)- potassiumylidene))propanamide carbonate 6-5 43 mg (0.21 mmol) of 5- 50 mg (0.21mmol) of 35 mg Acetonitrile reflux, A 21 (bromomethyl)-2- 2,2,3,3,3-(0.25 mmol) 2 h chloropyrimidine pentafluoro-N- of (pyridin-2(1H)-potassium ylidene))propanamide carbonate  1-22 37 mg (0.11 mmol) of 2-49 mg (0.11 mmol) of 12 mg THF Room D 31 chloro-N-[1-((6- phosphorus(0.11 mmol) temperature, 4 h chloropyridin-3- pentasulfide ofyl)methyl)pyridin-2(1H)- sodium ylidene]-2,2- carbonatedifluoroacetamide  1-23 31 mg (0.085 mmol) of N- 38 mg (0.085 mmol) 9 mgTHF Room D 59 [1-((6-chloropyridin-3- of phosphorus (0.0854 mmol)temperature, 4 h yl)methyl)pyridin-2(1H)- pentasulfide ofylidene]-2,2,3,3,3- sodium pentafluoropropanamide carbonate  5-20 36 mg(0.11 mmol) of N- 49 mg (0.11 mmol) of 12 mg THF Room D 100[1-((6-chloro-5- phosphorus (0.11 mmol) temperature, fluoropyridin-3-pentasulfide of 4 h yl)methyl)pyridin-2(1H)- sodium ylidene]-2,2,2-carbonate trifluoroacetamide 5-3 65 mg (0.29 mmol) of 5- 50 mg (0.29mmol) of 48 mg Acetonitrile reflux, 3 h A 38 (bromomethyl)-2-chloro-2,2-difluoro-N- (0.35 mmol) 3-fluoropyridine (pyridin-2(1H)- ofylidene))acetamide potassium carbonate 6-3 60 mg (0.29 mmol) of 5- 50 mg(0.29 mmol) of 48 mg Acetonitrile reflux, 3 h A 37 (bromomethyl)-2-2,2-difluoro-N- (0.35 mmol) chloropyrimidine (pyridin-2(1H)- ofylidene))acetamide potassium carbonate 8-2 73 mg (0.45 mmol) of 3- 97 mg(0.51 mmol) of 83 mg DMF 65° C., 3 h A 32 chloro-6- 2,2,2-trifluoro-N-(0.60 mmol) (chloromethyl)pyridazine (pyridin-2(1H)- ofylidene))acetamide potassium carbonate 5-4 54 mg (0.24 mmol) of 5- 50 mg(0.24 mmol) of 41 mg Acetonitrile reflux, 6 h A 51(bromomethyl)-2-chloro- 2-chloro-2,2- (0.30 mmol) 3-fluoropyridinedifluoro-N-(pyridin- of 2(1H)- potassium ylidene))acetamide carbonate4-4 60 mg (0.24 mmol) of 2- 50 mg (0.24 mmol of 41 mg Acetonitrilereflux, 6 h A 48 bromo-5- 2-chloro-2,2- (0.30 mmol) bromomethylpyridinedifluoro-N-(pyridin- of 2(1H)- potassium ylidene))acetamide carbonate6-4 49 mg (0.24 mmol) of 5- 50 mg (0.24 mmol) of 41 mg Acetonitrilereflux, 6 h A 55 (bromomethyl)-2- 2-chloro-2,2- (0.30 mmol)chloropyrimidine difluoro-N-(pyridin- of 2(1H)- potassiumylidene))acetamide carbonate 4-5 65 mg (0.26 mmol) of 2- 50 mg (0.26mmol) of 41 mg Acetonitrile reflux, 2 h A 8 bromo-5- 2,2,3,3,3- (0.30mmol) bromomethylpyridine pentafluoro-N- of (pyridin-2(1H)- potassiumylidene))propanamide carbonate

TABLE 44 Reaction Compound Base and the temperature, Method Yield No.Raw material 1 Raw material 2 like Solvent Time (Table) (%) 2-20 70 mg(0.22 mmol) of N- 107 mg (0.24 mmol) 25 mg (0.24 mmol) THF Room D 11[1-((2-chlorothiazol-5- of phosphorus of temperature, yl)methyl)pyridin-pentasulfide sodium 4 h 2(1H)-ylidene]-2,2,2- carbonatetrifluoroacetamide 10-20  130 mg (0.37 mmol) of 181 mg (0.41 mmol) 43 mg(0.41 mmol) THF Room D 93 2,2,2-trifluoro-N-[1- of phosphorus oftemperature, ((6- pentasulfide sodium 4 h trifluoromethyl)pyridin-carbonate 3-yl)methyl)pyridin- 2(1H)-ylidene]- acetamide 3-4  110 mg(0.58 mmol) of 105 mg (0.51 mmol) 103 mg (0.75 mmol) DMF 65° C., 2 h A63 2-fluoro-5- of 2-chloro-2,2- of (bromomethyl)pyridine difluoro-N-potassium (pyridin-2(1H)- carbonate ylidene))acetamide 3-5  110 mg (0.58mmol) of 139 mg (0.58 mmol) 88 mg (0.63 mmol) DMF 65° C. 2 h A 222-fluoro-5- of 2,2,3,3,3- of (bromomethyl)pyridine pentafluoro-N-potassium (pyridin-2(1H)- carbonate ylidene)propanamide 11-20  40 mg(0.15 mmol) of 65 mg (0.11 mmol) 16 mg (0.15 mmol) THF Room D 532,2,2-trifluoro-N-[1- of phosphorus of temperature, ((tetrahydrofuran-3-pentasulfide sodium 4 h yl)methyl)pyridin- carbonate2(1H)-ylidene]acetamide 1-14 200 mg (0.78 mmol) of 76 μl (0.94 mmol) 32μl (0.23 mmol) Acetonitrile reflux, 1 h B 28 1-[(6-chloropyridin-3- ofacrylic acid of yl)methyl]pyridin- chloride triethylamine 2(1H)-iminehydrochloride 1-37 78 mg (0.28 mmol) of N- 125 mg (0.28 mmol) 30 mg(0.28 mmol) THF Room D 21 [1-((6-chloropyridin-3- of phosphorus oftemperature, yl)methyl)pyridin- pentasulfide sodium 2 h 2(1H)-ylidene]-carbonate propionamide 1-39 180 mg (0.96 mmol) of 341 mg (0.75 mmol) 102mg (0.96 mmol) THF Room D 29 N-[1-((6-chloropyridin- of phosphorus oftemperature, 3-yl)methyl)pyridin- pentasulfide sodium 2 h2(1H)-ylidene]- carbonate isobutyramide 1-40 54 mg (0.19 mmol) of N- 54mg (0.19 mmol) 20 mg (0.19 mmol) THF Room D 12 [1-((6-chloropyridin-3-of phosphorus of temperature, yl)methyl)pyridin- pentasulfide sodium 2 h2(1H)-ylidene]- carbonate cyclopropane carboxyamide 1-15 200 mg (0.78mmol) of 1- 83 mg (0.94 mmol) 320 μl (2.34 mmol) Acetonitrile reflux, 5h B 19 [(6-chloropyridin-3- of propyol of yl)methyl]pyridin-2(1H)-oxychloride triethylamine imine hydrochloride 1-35 26 mg (0.074 mmol) ofN- 26 mg (0.06 mmol) 8 mg (0.074 mmol) THF Room D 23[1-((6-chloropyridin-3- of phosphorus of temperature,yl)methyl)pyridin-2(1H)- pentasulfide sodium 1.5 h ylidene]-3- carbonatephyenylpropanamide  1-501 100 mg (0.30 mmol) of N- 145 mg (1.50 mmol)205 μl (1.50 mmol) Ethanol 50° C., 19.5 h F 14 [1-((6-chloropyridin-3-of O-ethyl of yl)methyl)pyridin-2(1H)- hydroxylamine triethylamineylidene]-2,2,2- hydrochloride trifluoroethanethioamide  1-499 1.00 g(3.00 mmol) of N- 1.04 g (15.0 mmol) 2.00 ml (15.0 mmol) Ethanol 50° C.,21 h F 63 [1-((6-chloropyridin-3- of hydroxylamine ofyl)methyl)pyridin-2(1H)- hydrochloride triethylamine ylidene]-2,2,2-trifluoroethanethioamide  1-510 1.00 g (3.00 mmol) of N- 239 mg (1.50mmol) 205 μl (1.50 mmol) Ethanol 50° C., 19.5 h F 20[1-((6-chloropyridin-3- of O-benzyl of yl)methyl)pyridin-2(1H)-hydroxylamine triethylamine ylidene]-2,2,2- hydrochloridetrifluoroethanethioamide  1-511 30 mg (0.09 mmol) of N- 20 μl (0.28mmol) 38 μl (0.28 mmol) Acetonitrile Room G 72 [1-((6-chloropyridin-3-of acetyl chloride of temperature, yl)methyl)pyridin- triethylamine 15min 2(1H)-ylidene]-2,2,2- trifluoro-N′- hydroxyacetimidamide

TABLE 45 Com- Reaction pound Base and the temperature, Method Yield No.Raw material 1 Raw material 2 like Solvent Time (Table) (%) 1-519 30 mg(0.09 mmol) of 20 μl (0.17 mmol) 24 μl (0.17 mmol) Acetonitrile Room G67 N-[1-((6- of of temperature, chloropyridin-3- benzoyl triethylamine10 min yl)methyl)pyridin- chloride 2(1H)-ylidene]-2,2,2- trifluoro-N′-hydroxyacetimidamide 1-523 30 mg (0.09 mmol) of 20 μl (0.26 mmol) 36 μl(0.26 mmol) Acetonitrile Room G 49 N-[1-((6- of methyl of temperature,chloropyridin-3- chloroformate triethylamine 20 min yl)methyl)pyridin-2(1H)-ylidene]-2,2,2- trifluoro-N′- hydroxyacetimidamide 1-528 30 mg(0.09 mmol) of 20 μl (0.18 mmol) 25 μl (0.18 mmol) Acetonitrile Room G100 N-[1-((6- of of temperature, chloropyridin-3- methanesulfonyltriethylamine 20 min yl)methyl)pyridin- chloride 2(1H)-ylidene]-2,2,2-trifluoro-N′- hydroxyacetimidamide 1-531 30 mg (0.09 mmol) of 28 mg(0.15 mmol) 21 μl (0.15 mmol) Acetonitrile Room G 100 N-[1-((6- of 4- oftemperature, chloropyridin-3- methylbenzenesufonyl triethylamine 12 hyl)methyl)pyridin- chloride 2(1H)-ylidene]- 2,2,2-trifluoro-N′-hydroxyacetimidamide 1-507 30 mg (0.09 mmol) of 50 mg (0.45 mmol) 62 μl(0.45 mmol) Ethanol 50° C., 5 h F 45 N-[1-((6- of O- of chloropyridin-3-allyl triethylamine, yl)methyl)pyridin- hydroxylamine 25 mg (0.09 mmol)2(1H)-ylidene]- hydrochloride of 2,2,2- silver trifluoroethanethioamidecarbonate 1-516 30 mg (0.09 mmol) of 20 μl (0.25 mmol) 34 μl (0.25 mmol)Acetonitrile Room G 64 N-[1-((6- of of temperature, chloropyridin-3-acryloyl triethylamine 20 min yl)methyl)pyridin- chloride2(1H)-ylidene]- 2,2,2-trifluoro-N′- hydroxyacetimidamide 1-518 30 mg(0.09 mmol) of 15 mg (0.18 mmol) EDC- Dichloromethane Room G 22N-[1-((6- of 3- HCl 135 mg(0.18 mmol), temperature, chloropyridin-3-butynoate DMAP 22 mg(0.18 mmol) 21 h yl)methyl)pyridin- 2(1H)-ylidene]-2,2,2-trifluoro-N′- hydroxyacetimidamide 1-527 30 mg (0.09 mmol) of 20μl (0.16 mmol) 22 μl (0.16 mmol) Acetonitrile Room G 54 N-[1-((6- ofphenyl of temperature, chloropyridin-3- chloroformate triethylamine 1.5h yl)methyl)pyridin- 2(1H)-ylidene]- 2,2,2-trifluoro-N′-hydroxyacetimidamide 1-521 30 mg (0.09 mmol) of 20 mg (0.14 mmol) 40 μl(0.28 mmol) Acetonitrile Room G 46 N-[1-((6- of of temperature,chloropyridin-3- nicotinic acid triethylamine 1.5 h yl)methyl)pyridin-chloride 2(1H)-ylidene]- hydrochloride 2,2,2-trifluoro-N′-hydroxyacetimidamide 1-43  100 mg (0.30 mmol) Ethylamine (30% 90 μl(0.60 mmol) Ethanol 50° C., 1.5 h E 57 of N-[1-((6- methanol ofchloropyridin-3- solution, 0.60 mmol) triethylamine, yl)methyl)pyridin-91 mg (0.33 mmol) 2(1H)-ylidene]- of 2,2,2- silvertrifluoroethanethioamide carbonate 1-536 50 mg (0.15 mmol) of 20 μl(0.17 mmol) tBuOK Acetonitrile Room H 30 N-[1-((6- of benzyl 5 mg(0.04mmol) temperature, chloropyridin-3- isocyanate 1 h yl)methyl)pyridin-2(1H)-ylidene]- 2,2,2-trifluoro-N′- hydroxyacetimidamide

TABLE 46 Reaction Compound Base and the temperature, Method Yield No.Raw material 1 Raw material 2 like Solvent Time (Table) (%) 1-42 150 mg(0.45 mmol) of N- Methylamine 124 mg (0.45 mmol) Methanol 50° C., 1 h E56 [1-((6-chloropyridin-3- (40% methanol of yl)methyl)pyridin-2(1H)-solution, silver ylidene]-2,2,2- 1.36 mmol) carbonatetrifluoroethanethioamide 1-500 50 mg (0.15 mmol) of N- 63 mg (0.75 mmol)103 μl (0.75 mmol) Ethanol 50° C., 5 h F 50 [1-((6-chloropyridin-3- ofO- of yl)methyl)pyridin-2(1H)- methyl triethylamine, ylidene]-2,2,2-hydroxylamine 41 mg (0.15 mmol) trifluoroethanethioamide hydrochlorideof silver carbonate 1-504 50 mg (0.15 mmol) of N- 95 mg (0.75 mmol) 165μl (1.20 mmol) Ethanol 50° C., 5 h F 19 [1-((6-chloropyridin-3- of O-t-of yl)methyl)pyridin-2(1H)- butyl triethylamine, ylidene]-2,2,2-hydroxylamine 62 mg (0.23 mmol) trifluoroethanethioamide hydrochlorideof silver carbonate 1-534 40 mg (0.12 mmol) of N- 11 mg (0.13 mmol)tBuOK 4 mg (0.04 mmol) Acetonitrile Room H 32 [1-((6-chloropyridin-3- ofn- temperature, yl)methyl)pyridin-2(1H)- propyl 1 hylidene]-2,2,2-trifluoro- isocyanate N′-hydroxyacetimidamide 1-535 40 mg(0.12 mmol) of N- 14 mg (0.13 mmol) tBuOK 4 mg (0.04 mmol) AcetonitrileRoom H 54 [1-((6-chloropyridin-3- of temperature,yl)methyl)pyridin-2(1H)- chloroethyl 1 h ylidene]-2,2,2-trifluoro-isocyanate N′-hydroxyacetimidamide 1-72 150 mg (0.45 mmol) of N- 74 μl(0.68 mmol) 137 mg (0.50 mmol) Ethanol 50° C., 3 h E 45[1-((6-chloropyridin-3- of of silver yl)methyl)pyridin-2(1H)-benzylamine carbonate ylidene]-2,2,2- trifluoroethanethioamide 1-150 100mg (0.30 mmol) of N- 56 μl (0.60 mmol) 91 mg (0.33 mmol) Ethanol 50° C.,5 h E 50 [1-((6-chloropyridin-3- of of silver yl)methyl)pyridin-2(1H)-methylthioethylamine carbonate ylidene]-2,2,2- trifluoroethanethioamide1-67 100 mg (0.30 mmol) of N- 74 μl (1.20 mmol) 91 mg (0.33 mmol)Ethanol 50° C., 2 h E 49 [1-((6-chloropyridin-3- of 2- of silveryl)methyl)pyridin-2(1H)- aminoethanol carbonate ylidene]-2,2,2-trifluoroethanethioamide 1-515 30 mg (0.09 mmol) of N- 40 μl (0.44 mmol)30 μl (0.22 mmol) Acetonitrile 50° C., 2 h G 67 [1-((6-chloropyridin-3-of of yl)methyl)pyridin-2(1H)- cyclopropanecarboxylic triethylamineylidene]-2,2,2-trifluoro- acid chloride N′-hydroxyacetimidamide 1-56 100mg (0.30 mmol) of N- 38 μl (0.60 mmol) 91 mg (0.33 mmol) Ethanol 50° C.,2 h → E 57 [1-((6-chloropyridin-3- of of silver reflux, 2 hyl)methyl)pyridin-2(1H)- propargylamine carbonate ylidene]-2,2,2-trifluoroethanethioamide 1-512 30 mg (0.09 mmol) of N- 20 μl (0.23 mmol)34 μl (0.25 mmol) Acetonitrile Room G 32 [1-((6-chloropyridin-3- of oftemperature, yl)methyl)pyridin-2(1H)- propionyl triethylamine 30 minylidene]-2,2,2-trifluoro- chloride N′-hydroxyacetimidamide 1-514 30 mg(0.09 mmol) of N- 20 μl (0.19 mmol) 27 μl (0.20 mmol) Acetonitrile RoomG 61 [1-((6-chloropyridin-3- of of temperature, yl)methyl)pyridin-2(1H)-isopropionyl triethylamine 2 h ylidene]-2,2,2-trifluoro- chlorideN′-hydroxyacetimidamide 1-50 100 mg (0.30 mmol) of N- 48 μl (1.20 mmol)91 mg (0.33 mmol) Ethanol 50° C., 1.5 h → E 44 [1-((6-chloropyridin-3-of of silver reflux, 4.5 h yl)methyl)pyridin-2(1H)- cyclopropylaminecarbonate ylidene]-2,2,2- trifluoroethanethioamide

TABLE 47 Reaction Compound Base and temperature, Method Yield No. Rawmaterial 1 Raw material 2 the like Solvent Time (Table) (%) 1-114 80 mg(0.30 mmol) of N- 48 μl (0.36 mmol) of 73 mg Ethanol 50° C., 3.5 h E 52[1-((6-chloropyridin-3- 2- (0.33 mmol) yl)methyl)pyridin-2(1H)-phenyloxyethylamine of ylidene]-2,2,2- silver trifluoroethanethioamidecarbonate 1-44 80 mg (0.30 mmol) of N- 60 μl (0.72 mmol) of 73 mgEthanol 50° C., 2 h E 55 [1-((6-chloropyridin-3- n-propylamine (0.33mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-118 100 mg (0.30 mmol) of N- 62 μl(0.60 mmol) of 91 mg Ethanol 50° C., 5 h E 70 [1-((6-chloropyridin-3- 2-(0.33 mmol) yl)methyl)pyridin-2(1H)- aminomethylpyridine ofylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-119 100 mg(0.30 mmol) of N- 62 μl (0.60 mmol) of 91 mg Ethanol 50° C., 5 h E 58[1-((6-chloropyridin-3- 3- (0.33 mmol) yl)methyl)pyridin-2(1H)-aminomethylpyridine of ylidene]-2,2,2- silver trifluoroethanethioamidecarbonate 1-47 100 mg (0.30 mmol) of N- 44 mg (0.60 mmol) of 91 mgEthanol 50° C., 5 h E 49 [1-((6-chloropyridin-3- n-butylamine (0.33mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-55 100 mg (0.30 mmol) of N-CH2═CHCH2NH2 34 mg 91 mg Ethanol 50° C., 2 h → E 53[1-((6-chloropyridin-3- (0.60 mmol) (0.33 mmol) reflux, 1 hyl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-122 100 mg (0.30 mmol) of N-H2NCH2-(2-thienyl) 91 mg Ethanol 50° C., 2 h → E 30[1-((6-chloropyridin-3- 68 mg(0.60 mmol) (0.33 mmol) reflux, 1 hyl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-45 100 mg (0.30 mmol) of N- 70 mg(1.20 mmol) of 91 mg Ethanol 50° C., 2 h → E 35 [1-((6-chloropyridin-3-isopropylamine (0.33 mmol) reflux, 5 h yl)methyl)pyridin-2(1H)- ofylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-124 100 mg(0.30 mmol) of N- H2NCH2-(2-furanyl) 91 mg Ethanol 50° C., 2.5 h E 56[1-((6-chloropyridin-3- 58 mg(0.60 mmol) (0.33 mmol)yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-126 100 mg (0.30 mmol) of N-H2NCH2-(2- 91 mg Ethanol 50° C., 1 h E 43 [1-((6-chloropyridin-3-thienyldrofuranyl) (0.33 mmol) yl)methyl)pyridin-2(1H)- 61 mg(0.60 mmol)of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-64 100 mg(0.30 mmol) of N- 110 mg (1.20 mmol) 91 mg Ethanol 50° C., 1 h → E 22[1-((6-chloropyridin-3- of aminoacetonitrile (0.33 mmol) reflux, 6 hyl)methyl)pyridin-2(1H)- hydrochloride of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-146 100 mg (0.30 mmol) of N-CH3OCH2CH2NH2 91 mg Ethanol 50° C., 5 h E 30 [1-((6-chloropyridin-3- 45mg(0.60 mmol) (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2-silver trifluoroethanethioamide carbonate 1-52 100 mg (0.30 mmol) of N-51 mg (0.60 mmol) of 91 mg Ethanol 50° C., 4 h E 30[1-((6-chloropyridin-3- cyclopentylamine (0.33 mmol)yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-121 100 mg (0.30 mmol) of N- 65 mg(0.60 mmol) of 91 mg Ethanol 60° C., 4 h E 33 [1-((6-chloropyridin-3-4-aminomethyl (0.33 mmol) yl)methyl)pyridin-2(1H)- pyridine ofylidene]-2,2,2- silver trifluoroethanethioamide carbonate

TABLE 48 Reaction Compound Base and temperature, Method Yield No. Rawmaterial 1 Raw material 2 the like Solvent Time (Table) (%) 1-53 100 mg(0.30 mmol) of N- 59 mg (0.60 mmol) of 91 mg Ethanol 60° C., 2 h E 28[1-((6-chloropyridin-3- cyclohexylamine (0.33 mmol)yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silvertrifluoroethanethioamide carbonate 1-76 100 mg (0.30 mmol) of N- 73 mg(0.60 mmol) of 91 mg Ethanol 60° C., 4 h E 60 [1-((6-chloropyridin-3-phenethylamine (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2-silver trifluoroethanethioamide carbonate

TABLE 49 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹)266-2   5.62 (2H, s), 7.33 (1H, d), 7.83 m/z = 323 (1H, d), 8.57 (2H, m)(M + H) 444-2   5.73 (2H, s), 7.69 (1H, s), 8.56 m/z = 329 (1H, s) (M +H) 190-2   5.39 (2H, s), 6.87 (1H, dd), m/z = 317 7.36 (1H, d), 7.91(1H, dd), (M + H) 8.39 (1H, d), 8.49 (1H, s), 8.79 (1H, d) 201-2   5.45(2H, s), 7.37 (1H, d), 7.65 m/z = 317 (1H, d), 7.87 (1H, dd), 7.99 (M +H) (1H, d), 8.49 (1H, d), 9.80 (1H, d) 223-2   5.69 (2H, s), 7.31 (1H,d), 7.55 m/z = 317 (1H, dd), 7.92 (1H, dd), 8.28 (M + H) (1H, dd), 8.59(1H, d), 8.78 (1H, dd) 146-2   5.64 (2H, s), 7.14 (1H, dd), m/z = 3327.33 (1H, d), 7.47 (1H, dd), (M + H) 7.71 (1H, dd). 7.74 (1H, dd), 8.42(1H, d), 11.64 (1H, br s) 224-2   5.78 (2H, s), 7.57, 7.63 (1H, m/z =323 dd × 2), 7.70 (1H, s), 8.26, 8.41 (M + H) (1H, dd × 2), 8.82, 9.04(1H, dd × 2) 102-2   5.56 (2H, s), 7.15 (1H, m), 7.38 m/z = 341 (1H, d),7.84 (1H, dd), 8.26 (M + H) (1H, dd), 8.48 (1H, d), 8.60 (1H, d) 212-2  5.43 (2H, s), 7.35 (1H, d), 7.87 m/z = 317 (1H, dd), 8.20 (1H, d), 8.29(M + H) (1H, d), 8.51 (1H, d), 8.77 (1H, s) 1-20 5.48 (2H, s), 7.12 (1H,td), m/z = 332 7.34 (1H, d), 7.77 (1H, dd), (M + H) 7.96 (1H, m), 8.05(1H, dd), 8.45 (1H, d), 8.56 (1H, d) 12-2  5.54 (2H, s), 6.96 (1H, m),7.21 m/z = 316 (1H, d), 7.87 (1H, m), 7.97 (1H, (M + H) m), 8.34 (1H,d), 8.50 (1H, d) 213-2   5.51 (2H, s), 7.69 (1H, s), 8.25 m/z = 323 (1H,d), 8.30 (1H, d), 8.57 (1H, (M + H) s) 1-17 4.52 (2H, q), 5.44 (2H, s),6.85 m/z = 346 (1H, td), 7.31 (1H, d), 7.57 (2H, (M + H) m), 7.79 (1H,dd), 8.14 (1H, d), 8.40 (1H, d) 1-18 1.44 (3H, d), 5.31 (1H, m), 5.42m/z = 360 (2H, q), 6.54 (1H, td), 7.30 (1H, (M + H) d), 7.53 (2H, m).7.79 (1H, dd), 8.10 (1H, d), 8.40 (1H, d) 1-19 5.47 (2H, s), 5.81 (1H,m), 6.69 m/z = 414 (1H, m), 7.31 (1H, d), 7.65 (1H, (M + H) m), 7.68(1H, dd), 7.85 (1H, dd), 8.17 (1H, d), 8.40 (1H, d) 7-2  5.57 (2H, s),6.91 (1H, m), 7.80 (1H, m), 8.10 (1H, m), 8.47 (1H, s), 8.49 (1H, d),8.72 (1H, d) 1-13 3.22 (2H, q), 5.46 (2H, s), 6.65 m/z = 330 (1H, td),7.31 (1H, d), 7.62 (1H, (M + H) m), 7.66 (1H, dd). 7.70 (1H, dd), 8.35(1H, d), 8.41 (1H, d) 168-2   5.11 (2H, s), 7.40 (2H, m), 7.75 m/z =332.0426 (1H, dd), 8.09 (1H, d), 8.15 (1H, (M + H) d), 8.46 (1H, d),8.81 (1H, br s) 1-21 5.49 (2H, s), 6.21 (1H, t), 7.05 m/z = 314.0346(1H, td), 7.34 (1H, d), 7.82 (1H, (M + H) dd), 7.90 (1H, m), 7.94 (1H,dd), 8.45 (1H, d), 8.49 (1H, d) 3-20 5.51 (2H, s), 6.95 (1H, d), 7.15m/z = 316.0559 (1H, td), 7.96 (2H, m), 8.09 (1H, (M + H) d), 8.29 (1H,d), 8.52 (1H, d) 4-20 5.47 (2H, s), 7.13 (1H, m), 7.50 m/z = 375.9 (1H,m), 7.66 (1H, m), 7.97 (1H, (M + H) m), 8.07 (1H, m), 8.43 (1H, s), 8.54(1H, m) 3-3  5.54 (2H, s), 5.92 (1H, t), 6.79 (1H, td), 6.94 (1H, dd),7.70 (1H, m), 7.78 (1H, dd), 8.03 (1H, td), 8.30 (1H, d), 8.50 (1H, d)4-3  5.50 (2H, s), 5.90 (1H, t), 6.79 m/z = 342 (1H, m), 7.48 (1H, d),7.74 (3H, (M + H) m), 8.43 (1H, d), 8.50 (1H, d) 5-5  5.56 (2H, s), 6.91(1H, m), 7.69 m/z = 384.0372 (1H, dd), 7.82 (2H, m), 8.26 (1H, (M + H)d), 8.60 (1H, d) 6-5  5.52 (2H, s), 6.93 (1H, m), 7.86 m/z = 367.0687(2H, m). 8.61 (1H, d), 8.75 (2H, (M + H) s) 1-22 5.49 (2H, s), 7.09 (1H,td), m/z = 347.9972 7.35 (1H, d), 7.78 (1H, dd), (M + H) 7.95 (2H, m),8.46 (1H, d), 8.55 (1H, d) 1-23 5.47 (2H, s), 7.10 (1H, td), m/z =382.0246 7.34 (1H, d), 7.68 (1H, dd), (M + H) 7.95 (2H, m), 8.41 (1H,d), 8.55 (1H, dd) 5-20 5.49 (2H, s), 7.10 (1H, m), 7.65 m/z = 350.0188(1H, dd), 7.96 (1H, m), 8.00 (M + H) (1H, m), 8.27 (1H, d), 8.63 (1H, d)5-3  5.53 (2H, s), 5.90 (1H, t), 6.80 m/z = 316.0507 (1H, td), 7.76 (2H,m), 8.29 (M + H) (1H, d), 8.52 (1H, d)

TABLE 50 MS or IR Compound (KBr, v. No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹) 6-35.45 (2H, s), 5.89 (1H, t), 6.83 m/z = 299.0532 (1H, td), 7.75 (1H, m),7.82 (M + H) (1H, dd), 8.52 (1H, d), 8.81 (2H, s) 8-2 5.73 (2H, s), 6.90(1H, td), 7.54 (1H, d), 7.81 (1H, td), 7.97 (1H, d), 8.22 (1H, d), 8.53(1H, d) 5-4 5.54 (2H, s), 6.86 (1H, td), m/z = 350.0082 7.99 (3H, m).8.30 (1H, d), 8.54 (M + H) (1H, d) 4-4 5.52 (2H, s), 6.86 (1H, td), m/z= 375.96 7.49 (1H, d), 7.77 (2H, m), 7.83 (M + H) (1H, dd), 8.45 (1H,d), 8.52 (1H, d) 6-4 5.49 (2H, s), 6.90 (1H, td), m/z = 333.0121 7.82(1H, td), 7.87 (1H, dd), (M + H) 8.54 (1H, d), 8.81 (2H, s) 4-5 5.53(2H, s), 6.89 (1H, td), m/z = 410 7.48 (1H, d), 7.70 (1H, dd), (M + H)7.82 (2H, m), 8.41 (1H, d), 8.58 (1H, d)  2-20 5.57 (2H, s), 7.12 (1H,m), 7.68 m/z = 338 (1H, s), 7.97 (1H, m), 8.12 (1H, (M + H) d), 8.67(1H, d) 10-20 5.58 (2H, s), 7.12 (1H, m), 7.70 m/z = 366 (1H, d), 7.97(2H, m), 8.02 (1H, (M + H) d), 8.62 (1H, d), 8.77 (1H, s) 3-4 5.55 (2H,s), 6.86 (1H, td), m/z = 316 6.95 (1H, dd), 7.77 (1H, td), (M + H) 7.85(1H, dd), 8.06 (1H, td), 8.31 (1H, d), 8.53 (1H, d) 3-5 5.56 (2H, s),6.89 (1H, m), 6.94 m/z = 350 (1H, dd), 7.80 (2H, m), 7.97 (M + H) (1H,td), 8.27 (1H, d), 8.58 (1H. d) 11-20 1.69 (1H, m), 2.07 (1H, m), 2.84m/z = 291 (1H, m), 3.59 (1H, dd), 3.71 (M + H) (1H, dd), 3.77 (1H, m),3.96 (1H, m), 4.13 (1H, dd), 4.42 (1H, dd), 7.11 (1H, m), 7.92 (1H, dd),7.98 (1H, m), 8.40 (1H, d)  1-14 5.44 (2H, s), 5.61 (1H, dd), m/z = 2746.28 (1H, dd), 6.36 (1H, dd), (M + H) 6.52 (1H, m), 7.30 (1H, d), 7.52(1H, m), 7.57 (1H, d), 7.73 (1H, dd), 8.28 (1H, d), 8.44 (1H, d)  1-371.28 (3H, t), 2.88 (2H, q), 5.41 m/z = 292 (2H, s), 6.86 (1H, t), 7.35(1H, (M + H) d), 7.75 (3H, m), 8.10 (1H, d), 8.44 (1H, d)  1-39 1.26(6H, d), 2.55 (1H, m), 5.51 m/z = 306 (2H, s), 6.98 (1H, m), 7.36 (1H,(M + H) d), 7.76 (1H, dd), 7.77 (2H, m), 8.08 (1H, d), 8.44 (1H, d) 1-40 0.92 (2H, m), 1.22 (2H, m), 2.40 m/z = 304 (1H, m), 5.36 (2H, s),6.77 (1H, (M + H) td), 7.34 (1H, d), 7.66 (2H, m), 7.71 (1H, dd), 8.14(1H, d), 8.41 (1H, d)  1-15 5.08 (2H, d), 5.40 (2H, s), 5.84 m/z = 286(1H, t), 6.50 (1H, m), 7.30 (1H, (M + H) d), 7.50 (1H, m), 7.56 (1H, m),7.80 (1H, dd), 8.25 (1H, d), 8.47 (1H, d)  1-35 3.18 (4H, m), 5.05 (2H,s), 6.83 m/z = 368 (1H, td), 7.05 (1H, t), 7.25 (M + H) (2H, m), 7.38(3H, m), 7.59 (1H, dd), 7.67 (1H, d), 7.72 (1H, td), 7.99 (1H, d), 8.30(1H, d)  1-501 1.20 (3H, t), 4.10 (2H, q), 5.22 m/z = 359 (2H, s), 6.15(1H, td), 6.27 (M + H) (1H, d), 7.13 (1H, m), 7.27 (2H, m), 7.79 (1H,dd), 8.37 (1H, d)  1-499 5.26 (2H, s), 6.11 (1H, d), 6.31 m/z = 331 (1H,m), 7.31 (1H, m), 7.50 (1H, (M + H) d), 7.83 (1H, dd), 7.90 (1H, dd),8.44 (1H, d), 11.0 (1H, s)  1-510 5.07 (2H, s), 5.19 (2H, s), 6.13 m/z =421 (1H, td), 6.22 (1H, d), 7.07 (M + H) (1H, m), 7.18-7.40 (8H, m),7.69 (1H, dd), 8.34 (1H, d)  1-511 1.99 (3H, s), 5.27 (2H, s), 6.37 m/z= 373 (2H, m), 7.31 (2H, m), 7.44 (1H, (M + H) dd), 7.76 (1H, dd), 8.37(1H. d)  1-519 5.31 (2H, s), 6.36 (1H, t), 6.51 m/z = 435 (1H, d), 7.17(1H, d), 7.25 (4H, (M + H) m), 7.50 (3H, m), 7.78 (1H, dd), 8.41 (1H, d) 1-523 3.84 (3H, s), 5.26 (2H, s), 6.35 m/z = 389 (1H, m), 6.40 (1H, d),7.30 (2H, (M + H) m), 7.37 (1H, dd), 7.73 (1H, dd), 8.37 (1H, d)  1-5283.14 (3H, s), 5.27 (2H, s), 6.44 m/z = 409 (1H, td), 6.54 (1H, dd), 7.32(M + H) (1H, d), 7.41 (2H, m), 7.68 (1H, dd), 8.39 (1H, d)  1-531 2.45(3H, s), 5.23 (2H, s), 6.37 m/z = 485 (1H, d), 6.42 (1H, td), 7.29 (M +H) (4H, m), 7.45 (1H, d), 7.70 (1H, dd), 7.80 (2H, d), 8.35 (1H, d) 1-507 4.54 (2H, m), 5.16 (2H, m), 5.22 m/z = 371 (2H, s), 5.91 (1H, m),6.17 (1H, (M + H) td), 6.29 (1H, d), 7.15 (1H, m), 7.27 (2H, m), 7.79(1H, dd), 8.37 (1H, d)

TABLE 51 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹)1-516 5.27 (2H, s), 5.76 (1H, dd), 5.91 m/z = 385 (1H, dd), 6.22 (1H,dd), 6.36 (1H, (M + H) m), 6.42 (1H, d), 7.29 (2H, m), 7.42 (1H, d),7.76 (1H, dd), 8.37 (1H, d) 1-518 1.25 (1H, s), 1.98 (2H, s), 5.28 m/z =397 (2H, s), 6.38 (2H, m), 7.30 (2H, m), (M + H) 7.41 (1H, d), 7.75 (1H,dd), 8.38 (1H, d) 1-527 5.28 (2H, s), 6.39 (1H, m), 6.50 m/z = 451 (1H,d), 7.13 (1H, d), 7.22-7.41 (M + H) (7H, m), 7.76 (1H, dd), 8.40 (1H, d)1-521 5.30 (2H, s), 6.42 (1H, t), 6.52 m/z = 436 (1H, d), 7.20 (1H, d),7.32 (2H, m), (M + H) 7.53 (1H, dd), 7.75 (1H, dd), 8.01 (1H, dd), 8.41(1H, d), 8.54 (1H, d), 8.71 (1H, dd) 1-43 1.13(3H, t), 3.03 (2H, q),5.15 (2H, m/z = 343 s), 6.12 (1H, m), 6.19 (1H, d), (M + H) 7.14(1H, m),7.27 (1H, m), 7.33 (1H, d), 7.72 (1H, dd), 8.37 (1H, d) 1-536 4.48 (2H,d), 5.25 (2H, s), 6.36 m/z = 464 (1H, td), 6.41 (1H, d), 6.79 (1H, (M +H) m), 7.41 (7H, m), 7.73 (1H, dd), 8.40 (1H, d) 1-42 2.86 (3H, s), 5.16(2H, s), 6.15 m/z = 329 (2H, m), 7.16 (1H, m), 7.26 (1H, (M + H) dd),7.31 (1H, d), 7.73 (1H, dd), 8.38 (1H, d) 1-500 3.86 (3H, s), 5.22 (2H,s), 6.17 m/z = 345 (1H, m), 6.26 (1H, d), 7.14 (1H, m), (M + H) 7.23(1H, dd), 7.30 (1H, d), 7.78 (1H, dd), 8.39 (1H, d) 1-504 1.23 (9H, s),5.23 (2H, s), 6.10 m/z = 387 (1H, m), 6.22 (1H, d), 7.09 (1H, m), (M +H) 7.20 (1H, dd), 7.26 (1H, m), 7.79 (1H, dd), 8.35 (1H, d) 1-534 0.95(3H, t), 1.61 (2H, m), 3.23 m/z = 416 (2H, t), 5.24 (2H, s), 6.32 (1H,t), (M + H) 6.39 (1H, d), 6.48 (1H, m), 7.33 (3H, m), 7.74 (1H, dd),8.40 (1H, d) 1-535 3.65 (4H, m), 5.25 (2H, s), 6.36 m/z = 436 (1H, t),6.41 (1H, d), 6.82 (1H, (M + H) m), 7.36 (3H, m), 7.74 (1H, dd), 8.41(1H, d) 1-72 4.22 (2H, s), 5.13 (2H, s), 6.14 m/z = 405 (1H, m), 6.21(1H, d), 7.13 (1H, (M + H) m), 7.26 (7H, m), 7.68 (1H, dd), 8.36 (1H, d)1-150 2.08 (3H, s), 2.70 (2H, t), 3.22 m/z = 389 (2H, t), 5.15 (2H, s),6.16 (1H, (M + H) t), 6.22 (1H, d), 7.17 (1H, m), 7.29 (1H, d), 7.33(1H, d), 7.70 (1H, dd), 8.38 (1H, d) 1-67 3.13 (2H, m), 3.73 (2H, t),5.15 m/z = 359 (2H, s), 6.18 (2H, m), 7.17 (1H, (M + H) m), 7.33 (2H,m), 7.71 (1H, dd), 8.37 (1H, d) 1-515 0.82 (2H, m), 0.93 (2H, m), 1.40m/z = 399 (1H, m), 5.27 (2H, s), 6.35 (1H, (M + H) m), 6.42 (1H, d),7.31 (2H, m), 7.41 (1H, d), 7.77 (1H, dd), 8.38 (1H, d) 1-56 2.13 (1H,t), 3.85 (2H, d), 5.18 m/z = 353 (2H, s), 6.21 (1H, t), 6.25 (1H, (M +H) d), 7.18 (1H, m), 7.29 (1H, d), 7.33 (1H, d), 7.70 (1H, dd), 8.38(1H, d) 1-512 1.02 (3H, t), 2.23 (2H, q), 5.26 m/z = 387 (2H, s), 6.34(1H, m), 6.39 (1H, (M + H) m), 7.29 (2H, m), 7.40 (1H, d), 7.75 (1H,dd), 8.37 (1H, d) 1-514 0.97 (6H, s), 2.37 (1H, m), 5.26 m/z = 399 (2H,s), 6.35 (1H, m), 6.40 (1H, (M + H) d), 7.27 (2H, m), 7.42 (1H, dd),7.77 (1H, dd), 8.38 (1H, d) 1-50 0.74 (2H, m), 0.85 (2H, m), 2.51 m/z =355 (1H, m), 5.18 (2H, s), 6.12 (1H, (M + H) m), 6.30 (1H, d), 7.15 (1H,m), 7.27 (1H, m), 7.31 (1H, d), 7.79 (1H, dd), 8.39 (1H, d) 1-114 3.44(2H, td), 4.18 (2H, t), m/z = 435 5.14 (2H, s), 6.15 (1H, td), (M + H)6.26 (1H, d), 6.86 (2H, d), 6.92 (1H, m), 7.16 (1H, m), 7.28 (4H, m),7.71 (1H, dd), 8.38 (1H, d) 1-44 0.83 (3H, t), 1.55 (2H, m), 2.91 m/z =357 (2H, m), 5.14 (2H, s), 6.12 (1H, (M + H) td), 6.18 (1H, d), 7.13(1H, m), 7.30 (2H, m), 7.71 (1H, dd), 8.36 (1H, d) 1-118 4.41 (2H, s),5.15 (2H, s), 6.18 m/z = 406 (1H, t), 6.24 (1H, d), 7.14 (2H, (M + H)m), 7.26 (2H, m), 7.54 (1H, d), 7.68 (1H, dd), 7.71 (1H, dd), 8.38 (1H,d), 8.47 (1H, d) 1-119 4.22 (2H, s), 5.16 (2H, s), 6.20 m/z = 406 (2H,m), 7.15-7.30 (3H, m), 7.34 (M + H) (1H, dd), 7.61 (1H, d), 7.79 (1H,dd), 8.37 (1H, d), 8.42 (1H, d), 8.46 (1H, d)

TABLE 52 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹)1-47 0.85 (3H, t), 1.25 (2H, m), m/z = 371 1.53 (2H, m), 2.96 (2H, m),5.14 (2H, (M + H) s), 6.10 (1H, m), 6.17 (1H, d), 6.99 (1H, m), 7.27(2H, m), 7.70 (1H, dd), 8.36 (1H, d) 1-55 3.65 (2H, m), 5.04 (2H, m),m/z = 355 5.15 (2H, s), 5.90 (1H, m), 6.13 (1H, (M + H) m), 6.20 (1H,d), 7.13 (1H, m), 7.28 (2H, m), 7.71 (1H, dd), 8.36 (1H, d)  1-122 4.41(2H, s), 5.17 (2H, s), m/z = 411 6.17 (2H, m), 6.82 (1H, m), 6.91 (1H,(M + H) m), 7.16 (2H, m), 7.30 (2H, m), 7.70 (1H, dd), 8.38 (1H, d) 1-451.02 (6H, d), 3.34 (1H, m), m/z = 357 5.13 (2H, s), 6.10 (1H, m), 6.24(1H, (M + H) d), 7.11 (1H, m), 7.26 (1H, m), 7.31 (1H, d), 7.68 (1H,dd), 8.35 (1H, d)  1-124 4.20 (2H, s), 5.17 (2H, s), m/z = 395 6.13-6.29(4H, m), 7.17 (1H, m), (M + H) 7.30 (3H, m), 7.71 (1H, dd), 8.38 (1H, d) 1-126 1.49 (1H, m), 1.84 (2H, m), m/z = 399 1.99 (1H, m), 2.98 (1H,ddd), (M + H) 3.14 (1H, ddd), 3.73 (2H, m), 4.09 (1H, m), 5.13 (2H, m),6.13 (1H, m), 6.20 (1H, d), 7.14 (1H, m), 7.30 (2H, m), 7.70 (1H, dd),8.37 (1H, d) 1-64 4.01 (2H, s), 5.24 (2H, s), m/z = 354 6.34 (2H, m),7.34 (2H, m), 7.41 (1H, (M + H) dd), 7.66 (1H, dd), 8.36 (1H, d)  1-1463.21 (2H, m), 3.34 (2H, s), m/z = 373 3.57 (2H, t), 5.14 (2H, s), 6.15(1H, (M + H) m), 6.21 (1H, m), 7.15 (1H, m), 7.30 (2H, m), 7.72 (1H,dd), 8.37 (1H, d) 1-52 1.40-1.77 (8H, m), 3.48 (1H, m), m/z = 383 5.12(2H, s), 6.09 (1H, m), (M + H) 6.23 (1H, d), 7.12 (1H, m), 7.24 (1H, m),7.31 (1H, d), 7.69 (1H, dd), 8.35 (1H, d)  1-121 4.18 (2H, s), 5.14 (2H,s), m/z = 406 6.20 (2H, m), 7.19 (3H, m), 7.26 (1H, (M + H) m), 7.35(1H, dd), 7.75 (1H, dd), 8.36 (1H, d), 8.51 (2H, m) 1-53 0.98-1.72 (10H,m), 2.91 (1H, m/z = 397 m), 5.11 (2H, s), 6.11 (1H, td), (M + H) 6.24(1H, d), 7.11 (1H, m), 7.29 (3H, m), 7.66 (1H, dd), 8.34 (1H, d) 1-762.90 (2H, t), 3.24 (2H, td), m/z = 419 5.07 (2H, s), 6.01 (1H, d), (M +H) 6.09 (1H, td), 7.02-7.30 (8H, m), 7.61 (1H, dd), 8.34 (1H, d) 267-2  4.34 (1H, d), 4.62 (1H, d), 1730, 6.40 (1H, d), 7.20 (1H, d), 7.51 (2H,1689, m), 7.59 (1H, dd), 7.63 (2H, m), 1556, 7.82 (1H, d), 8.23 (1H, d)1467, 1440, 1418 253-2   5.31 (2H, s), 7.28 (2H, m), 1644, 7.50 (1H, d),7.72 (3H, m), 7.85 (1H, 1557, m), 8.25 (1H, d), 8.45 (1H, d) 1508, 1483251-2   5.20 (2H, s), 7.26 (2H, m), 3065, 7.63 (2H, m), 7.85 (2H, m),8.02 (1H, 1696, d), 8.23 (2H, m) 1463, 1403 13-2  5.76 (2H, s), 6.91(1H, m), 3060, 7.46 (1H, m), 7.60 (1H, m), 7.70 (1H, 2226, d), 7.80 (2H,m), 8.12 (1H, d), 1641, 8.53 (1H, d) 1556, 1509 1-1  5.49 (2H, s), 6.67(1H, m), — 7.30 (1H, m), 7.60 (1H, m), 7.72 (2H, m), 7.81 (1H, dd), 8.42(1H, d), 9.06 (1H, s) 1-41 5.64 (2H, s), 7.50 (2H, m), m/z = 315.16 7.70(1H, d), 7.78 (1H, dd), (M + H) 8.27 (1H, m), 8.37 (1H, d), 8.78 (1H, d)(methanol-d4)

TABLE 53 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹)2-2  2.47 (2H, m), 4.17 (2H, t), m/z = 322 5.07 (1H, d), 5.15 (1H, dd),5.39 (2H, (M + H) s), 5.85 (1H, m), 6.43 (1H, td), 7.30 (1H, d), 7.44(2H, m), 7.75 (1H, dd), 8.08 (1H, d), 8.40 (1H, d) 1-647 2.47 (2H, m),4.17 (2H, t), m/z = 5.07 (1H, d), 5.15 (1H, dd), 5.39 (2H, 318.1013 s),5.85 (1H, m), 6.43 (1H, td), (M + H) 7.30 (1H, d), 7.44 (2H, m), 7.75(1H, dd), 8.08 (1H, d), 8.40 (1H, d) 1-670 3.35 (2H, tdd), 5.17 (2H, s),m/z = 379 6.02 (1H, tt), 6.23 (2H, m), 7.22 (1H, (M + H) m), 7.33 (2H,m), 7.69 (1H, dd), 8.37 (1H, d) 157-2   5.51 (2H, s), 6.63 (1H, dd), m/z= 332 7.42 (1H, d), 7.77 (1H, d), 7.84 (1H, (M + H) dd), 8.26 (1H, d),8.45 (1H, d) 1-10  1.61 (1H, m), 2.29 (2H, m), m/z = 324 4.73 (2H, s),7.26 (1H, m), 7.31 (1H, m), (M + H) 7.69 (1H, m), 7.79 (1H, m), 8.23(1H, d), 8.40 (1H, d), 8.57 (1H, d) 580-2   5.47 (2H, s), 6.89 (1H, m),m/z = 332 7.47 (2H, m), 7.82 (2H, m), 8.41 (1H, s), (M + H) 8.56 (1H, d)1-671 0.87 (3H, t), 1.28 (10H, m), m/z = 427 1.55 (2H, m), 2.96 (2H, t),5.14 (2H, s), (M + H) 6.13 (1H, t), 6.18 (1H, d), 7.13 (1H, m), 7.30(2H, m), 7.71 (1H, dd), 8.37 (1H, d) 1-658 0.87 (3H, t), 1.25 (26H, m),m/z = 539 1.55 (2H, m), 2.96 (2H, t), 5.14 (2H, s), (M + H) 6.11 (1H,t), 6.17 (1H, d), 7.13 (1H, m), 7.30 (2H, m), 7.70 (1H, dd), 8.36 (1H,d) 1-659 0.87 (3H, t), 1.26 (18H, m), m/z = 483 1.53 (2H, m), 2.95 (2H,t), 5.14 (2H, s), (M + H) 6.12 (1H, t), 6.18 (1H, d), 7.13 (1H, m), 7.31(2H, m), 7.71 (1H, dd), 8.36 (1H, d) 1-660 0.74 (3H, t), 0.97 (3H, d),m/z = 371 1.42 (2H, m), 3.08 (1H, m), 5.12 (2H, (M + H) dd), 6.09 (1H,t), 6.23 (1H, d), 7.11 (1H, m), 7.24 (1H, m), 7.30 (1H, d), 7.67 (1H,dd), 8.35 (1H, d) 1-681 0.77, 0.90 (6H, t × 2), 1.40 (4H, m/z = 385 m),2.97 (1H, m), 5.11 (2H, s), (M + H) 6.10 (1H, t), 6.25 (1H, d), 7.11(1H, m), 7.24 (1H, d), 7.32 (1H, d), 7.66 (1H, dd), 8.34 (1H, d) 1-6860.81, 0.91 (6H, t × 2), m/z = 413 1.02-1.45 (8H, m), 3.19 (1H, m), 5.12(2H, (M + H) s), 6.10 (1H, t), 6.25 (1H, d), 7.11 (1H, m), 7.22 (1H, d),7.30 (1H, d), 7.64 (1H, dd), 8.33 (1H, d) 1-661 0.81 (3H, t), 0.97 (3H,d), m/z = 385 0.90-1.50 (4H, m), 3.19 (1H, m), (M + H) 5.07 (1H, d),5.15 (1H, d), 6.09 (1H, t), 6.24 (1H, d), 7.11 (1H, m), 7.27 (2H, m),7.66 (1H, dd), 8.34 (1H, d) 1-662 0.75 (3H, d), 0.80 (3H, d), m/z = 3850.94 (3H, d), 1.61 (1H, m), 2.86 (1H, (M + H) m), 5.11 (2H, s), 6.09(1H, t), 6.23 (1H, d), 7.11 (1H, t), 7.25 (1H, d), 7.30 (1H, d), 7.66(1H, dd), 8.34 (1H, d) 1-663 1.35 (3H, d), 4.33 (1H, q), m/z = 419 5.05(1H, d), 5.11 (1H, d), 6.00 (1H, (M + H) d), 6.08 (1H, t), 6.96 (1H, m),7.15-7.26 (7H, m), 7.63 (1H, dd), 8.33 (1H, d) 1-664 1.55-1.75 (3H, m),1.95 (1H, m), m/z = 445 2.70-2.88 (2H, m), 4.36 (1H, t), (M + H) 5.05(1H, d), 5.20 (1H, d), 6.13 (1H, t), 6.38 (1H, d), 6.96 (1H, m),7.02-7.20 (5H, m), 7.28 (1H, d), 7.62 (1H, dd), 8.3 (1H, d) 1-665 1.57(3H, d), 4.78 (1H, d), m/z = 469 4.91 (1H, d), 5.18 (1H, q), 5.80 (1H,(M + H) d), 5.93 (1H, t), 6.72 (1H, m), 7.05 (1H, d), 7.14 (1H, d), 7.38(3H, m), 7.54 (1H, dd), 7.62 (1H, d), 7.66 (1H, d), 7.80 (1H, d), 7.84(1H, d), 8.28 (1H, d) 1-666 0.74 (3H, t), 1.75 (2H, m), m/z = 433 4.03(1H, t), 5.06 (2H, dd), (M + H) 5.85 (1H, d), 6.05 (1H, m), 6.86 (1H,m), 7.10-7.28 (7H, m), 7.63 (1H, dd), 8.33 (1H, d) 1-667 1.34 (3H, d),4.45 (1H, q), m/z = 409 5.11 (1H, d), 5.16 (1H, d), 6.07 (1H, (M + H)m), 6.14 (1H, td), 6.26 (2H, m), 7.11 (1H, m), 7.28 (3H, m), 7.67 (1H,dd), 8.36 (1H, d) 1-676 5.06 (2H, s), 5.37 (1H, s), m/z = 481 5.38 (1H,d), 6.07 (1H, t), 6.85 (1H, (M + H) t), 7.10-7.28 (12H, m), 7.61 (1H,d), 8.33 (1H, s) 1-668 0.79 (9H, s), 0.85 (3H, d), m/z = 399 2.89 (1H,q), 5.11 (2H, s), 6.08 (1H, (M + H) t), 6.23 (1H, d), 7.10 (1H, t), 7.23(1H, d), 7.30 (1H, d), 7.65 (1H, d), 8.34 (1H, s)

TABLE 54 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹)47-2   5.68 (2H, d), 6.57 (1H, m), m/z = 334 7.34 (1H, d), 7.80 (1H, m),7.97 (1H, (M + H) dd), 8.39 (1H, d), 8.57 (1H, s) 91-2   5.92 (2H, s),6.95 (1H, d), m/z = 350 7.30 (1H, d), 7.69 (1H, m), 7.86 (1H, (M + H)dd), 8..49 (1H, dd), 8.53 (1H, d) 478-2   2.59 (3H, s), 5.77 (2H, s),m/z = 330 6.75 (1H, d), 7.31 (1H, d), 7.63 (1H, (M + H) dd), 7.72 (1H,m), 8.33 (1H, d), 8.45 (1H, d) 479-2   2.73 (3H, s), 5.71 (2H, s), m/z =336 6.73 (1H, d), 7.63 (1H, s), 7.69 (1H, (M + H) t), 8.44 (1H, d) 1-51 1.60 (2H, m), 1.73 (1H, m), m/z = 369 2.03 (4H, m), 3.75 (1H, m), 5.12(2H, (M + H) s), 6.12 (1H, t), 6.16 (1H, d), 7.10 (1H, m), 7.25 (1H, d),7.32 (1H, d), 7.71 (1H, dd), 8.37 (1H, d) 566-2   4.09 (3H, s), 5.71(2H, s), m/z = 346 6.25 (1H, d), 7.29 (1H, d), 7.74 (1H, (M + H) t),7.97 (1H, dd), 8.17 (1H, d), 8.50 (1H, d) 488-2   1.77 (1H, m), 2.11(1H, m), m/z = 289 2.62 (3H, s), 2.98 (1H, m), 3.53 (1H, (M + H) dd),3.67 (1H, dd), 3.78 (1H, m), 3.98 (1H, m), 4.22 (1H, m), 4.65 (1H, m),6.73 (1H, d), 7.66 (1H, t), 8.32 (1H, d) 511-2   5.58 (2H, s), 7.38 (1H,d), m/z = 361 7.86 (1H, dd), 8.40 (1H, dd), (M + H) 8.47 (1H, d), 8.55(1H, d), 8.93 (1H, d) 1-669 1.42 (3H, d), 4.65 (1H, q), m/z = 425 5.12(2H, s), 6.13 (2H, m), 6.75 (1H, (M + H) d), 6.88 (1H, dd), 7.07 (1H,m), 7.11 (1H, d), 7.26 (2H, m), 7.65 (1H, dd), 8.35 (1H, d) 179-2   5.30(2H, s), 6.43 (1H, dd), m/z = 332 6.66 (1H, dd), 7.40 (1H, d), (M + H)7.60 (2H, m), 8.20 (1H, d) 555-2   3.87 (3H, s), 5.60 (2H, s), m/z = 3467.51 (1H, d), 7.88 (1H, dd), (M + H) 7.93 (1H, dd), 8.34 (1H, d), 8.49(1H, d), 8.56 (1H, d) (DMSO-d6) 577-2   5.65 (2H, s), 6.87 (1H, td), m/z= 349 7.30 (1H, d), 7.81 (1H, m), (M + H) 8.08 (1H, dd), 8.13 (1H, d),8.54 (1H, d) 544-2   3.93 (3H, s), 5.45 (2H, s), m/z = 346 6.49 (1H,dd), 7.31 (1H, d), (M + H) 7.66 (1H, d), 7.83 (1H, dd), 8.13 (1H, d),8.42 (1H, d) 168-2   5.62 (2H, s), 7.43 (1H, d), m/z = 332 7.64 (1H,dd), 7.88 (1H, dd), (M + H) 7.94 (1H, d), 8.26 (1H, d), 8.49 (1H, d)1-644 4.18 (2H, s), 4.68 (2H, s), m/z = 368 5.36 (2H, s), 6.55 (1H, m),(M + H) 7.16 (1H, d), 7.29 (1H, d), 7.35 (2H, m), 7.40 (2H, m), 7.52(2H, m), 7.75 (1H, dd), 8.28 (1H, d), 8.40 (1H, d) 578-644  4.19 (2H,s), 4.69 (2H, s), m/z = 334 5.42 (2H, s), 6.52 (1H, m), (M + H) 7.20(1H, m), 7.30 (1H, m), 7.32 (2H, m), 7.40 (2H, m), 7.55 (2H, m), 7.72(1H, dd), 8.30 (1H, dd), 8.52 (1H, dd), 8.62 (1H, d) 1-703 5.20 (1H, d),5.45 (1H, d), 1715, 1636, 6.55 (1H, m) 7.34 (1H, m), 1552, 1505, 7.50(1H, m), 7.60 (1H, m), 1457, 1174, 7.79 (1H, dd), 8.39 (1H, d) 11441-707 5.43 (2H, s), 6.93 (1H, m), (EI-HRMS) 7.36 (1H, d), 7.77-7.85 (3H,m/z = 351.0084 m), 7.95 (1H, dd), 8.39 (1H, (M+) d) 1-706 1.20 (6H, m),2.67 (4H, m), m/z = 298 5.22 (2H, s), 6.52 (1H, m),. (M + H) 7.31 (1H,m), 7.51 (1H, m), 7.60 (1H, dd), 7.73 (1H, m), 7.84 (1H, d), 8.41 (1H,d) 1-692 1.11 (3H, t), 1.20 (3H, t), m/z = 356 3.76 (2H, m), 3.92 (2H,m), 6.58 (1H, (M + H) m), 7.26 (1H, d)., 7.53 (2H, m), 7.74 (1H, dd),8.12 (1H, d), 8.40 (1H, d) (DMSO-d6) 1-700 1.20 (6H, m), 2.67 (4H, m),m/z = 404 5.22 (2H, s), 6.52 (1H, m),. 7.31 (1H, (M + H) m), 7.51 (1H,m), 7.60 (1H, dd), 7.73 (1H, m), 7.84 (1H, d), 8.41 (1H, d) 1-701 0.95(6H, m), 1.56 (4H, m), m/z = 432 2.62 (4H, m), 5.18 (2H, s), 6.52 (1H,(M + H) m), 7.34 (1H, m), 7.49 (1H, m), 7.59 (1H, m), 7.77 (1H, dd),7.84 (1H, d), 8.42 (1H, d) 1-702 1.13-1.46 (m, 12H), 3.20 (m, 2H), m/z =432 5.27 (s, 2H), 6.51 (m, 1H), (M + H) 7.31 (m, 1H), 7.52 (m, 1H), 7.63(m, 1H), 7.78 (m, 2H), 8.43 (d, 1H) 1-646 1.31 (6H, d), 4.95 (1H, sep),1646, 5.40 (2H, s), 6.40 (1H, m), 1620, 7.28 (1H, d), 7.40 (2H, m), 7.73(1H, 1548, dd) 8.05 (1H, m), 8.40 (1H, d) 1504, 1453, 1-645 5.18 (2H,s), 5.37 (2H, s), 1655, 6.43 (1H, m), 7.25-7.36 (4H, m), 1518, 7.41-7.46(4H, m), 7.72 (1H, 1455, dd), 8.12 (1H, m), 8.38 (1H, d) 1399, 12351-643 5.52 (2H, s), 6.78 (1H, m), 1633, 7.31 (1H, d), 7.68-7.75 (3H, m),1601, 8.39 (1H, m), 8.56 (1H, s) 1541, 1502, 1482, 1453, 1384 2-643 5.51(2H, s), 6.80 (1H, m), 1632, 7.60 (1H, s), 7.75 (2H, m), 8.57 (1H, 1597,m) 1541, 1506, 1483, 1455, 1388

Further, the synthetic methods in the Table are described as follows.

A: the same method as in Synthetic Example 1

B: the same method as in Synthetic Example 2

C: the same method as in Synthetic Example 3

D: the same method as in Synthetic Example 4

E: the same method as in Synthetic Example 5

F: the same method as in Synthetic Example 6

G: the same method as in Synthetic Examples 7 and 8

H: the same method as in Synthetic Example 9

Preparation Example Preparation Example

Preparation Example 1 [Wettable powder] Compound P212 10% by weightImidacloprid 20% by weight Clay 50% by weight White carbon  2% by weightDiatomaceous earth 13% by weight Calcium ligninsulfonate  4% by weightSodium lauryl sulfate  1% by weight

The ingredients were homogeneously mixed and ground to obtain wettablepowder.

Preparation Example 2 [Water dispersible granule] Compound P212 10% byweight Imidacloprid 20% by weight Clay 60% by weight Dextrin  5% byweight Alkyl maleate copolymer  4% by weight Sodium lauryl sulfate  1%by weight

The ingredients were homogeneously ground and mixed, water was addedthereto to knead the ingredients thoroughly and then the mixture wasgranulated and dried to obtain water dispersible granules.

Preparation Example 3 [Flowables] Compound 1-20 5% by weightImidacloprid 20% by weight POE polystyrylphenyl ether sulfate 5% byweight Propylene glycol 6% by weight Bentonite 1% by weight 1%xanthan-gum aqueous solution 3% by weight PRONALEX-300 (TOHO Chemical0.05% by weight Industry Co., Ltd.) ADDAC827 (KI Chemical Industry Co.,0.02% by weight Ltd.) Water added to 100% by weight

All the ingredients except for the 1% xanthan-gum aqueous solution and asuitable amount of water were premixed together from the blending, andthe mixture was then ground by a wet grinder. Thereafter, the 1%xanthan-gum aqueous solution and the remaining water were added theretoto obtain 100% by weight of flowables.

Preparation Example 4 [Emulsifiable concentrate] Compound P212  2% byweight Imidacloprid 13% by weight N,N-dimethylformamide 20% by weightSolvesso 150 (Exxon Mobil Corporation) 55% by weight Polyoxyethylenealkyl aryl ether 10% by weight

The ingredients were homogeneously mixed and dissolved to obtain anemulsifiable concentrate.

Preparation Example 5 [Dust] Compound P212 0.5% by weight  Imidacloprid1.5% by weight  Clay 60% by weight Talc 37% by weight Calcium stearate 1% by weight

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 6 [DL Dust] Compound P212 1% by weight Tebufloquin1% by weight Ethofenprox 1% by weight DL clay 94.5% by weight   Whitecarbon 2% by weight Light liquid paraffin 0.5% by weight  

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 7 [Microgranule fine] Compound P212 1% by weightImidacloprid 1% by weight Carrier 94% by weight  White carbon 2% byweight Hisol SAS-296 2% by weight

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 8 [Granules] Compound 1-20  2% by weightChlorantraniliprole  1% by weight Bentonite 39% by weight Talc 10% byweight Clay 46% by weight Calcium ligninsulfonate  2% by weight

The ingredients were homogeneously ground and mixed, water was addedthereto to knead the ingredients thoroughly, and then the mixture wasgranulated and dried to obtain granules.

Preparation Example 9 [Microcapsules] Compound 1-20 2% by weightImidacloprid 3% by weight Urethane resin 25% by weight Emulsifier/Dispersant 5% by weight Antiseptic 0.2% by weight   Water64.8% by weight  

Microcapsules were obtained by forming a urethane resin coating on thesurface of particles of the compound represented by Formula (I) andimidacloprid particles using the ingredients by interfacialpolymerization.

Preparation Example 10 [Granules] Compound P212 2% by weight Probenazole24% by weight  Sodium lauryl sulfate 1% by weight Bentonite 2% by weightCalcium stearate 1% by weight PVA 2% by weight Clay 68% by weight 

The ingredients were homogeneously ground and mixed, water was addedthereto to knead the ingredients thoroughly, and then the mixture wasgranulated and dried to obtain granules.

Preparation Example 11 [Granules] Compound P212  2% by weightChlorantraniliprole  1% by weight Probenazole 24% by weight Bentonite40% by weight Talc 10% by weight Clay 21% by weight Calciumligninsulfonate  2% by weight

The ingredients were homogeneously ground and mixed, water was addedthereto to knead the ingredients thoroughly, and then the mixture wasgranulated and dried to obtain granules.

Preparation Example 12 [Liquid drops] Compound 1-20 10% by weightFipronil  1% by weight Benzyl alcohol 73.9% by weight   Propylenecarbonate 15% by weight BHT 0.1% by weight 

The ingredients were homogeneously stirred and dissolved to obtainliquid drops.

Preparation Example 13 [Liquid drops] Compound P212 48% by weightFipronil 2% by weight Ethanol 50% by weight

The ingredients were homogeneously mixed to obtain liquid drops.

Preparation Example 14 [Emulsifiable concentrate] Compound 1-20 5% byweight Etoxazole 5% by weight Xylene 35% by weight Dimethyl sulfoxide35% by weight

The ingredients were dissolved, and 14% by weight of polyoxyethylenestyryl phenyl ether and 6% calcium dodecylbenzenesulfonate were addedthereto, and the mixture was thoroughly stirred and mixed to obtain a10% emulsifiable concentrate.

Preparation Example 15 [Liquid drops] Compound P212 10% by weightEtoxazole 5% by weight Glycol (glycol mono alkyl ether) 85% by weightBHT or BHA appropriate amount

An appropriate amount of sorbitan monooleate or sorbitan monolaurate,caprylic acid monoglyceride or isostearic acid monoglyceride, orpropylene glycol monocaprylate was added to the ingredients, and alcoholor propylene carbonate, N-methyl-2-pyrrolidone or water was addedthereto to obtain liquid drops as 100% by weight.

Reference Test Example Foliar Treatment Test of Single Agent ReferenceTest Example 1 Pest Control Test of Plutella Xylostella

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage inpot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed to the leaf disk.After an air drying process, second instar larvae were released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and themortality of larvae was calculated by the following equation. Test induplicate.Mortality (%)={number of dead larvae/(number of survived larvae+numberof dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activityhaving a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 2 Pest Control Test of Spodoptera Litura

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage inpot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed to the leaf disk.After an air drying process, third instar larvae were released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and themortality of larvae was calculated by the following equation. Test induplicate.Mortality (%)={number of dead larvae/(number of survived larvae+numberof dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activityhaving a mortality of 80% or higher by a foliar treatment at 500 ppm.

Reference Test Example 3 Pest Control Test of Aphis Gossypii

A leaf disk having a diameter of 2.0 cm was cut out from a cucumber inpot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed to the leaf disk.After an air drying process, first instar larvae were released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and themortality of larvae was calculated by the following equation. Test induplicate.Mortality (%)={number of dead larvae/(number of survived larvae+numberof dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activityhaving a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 4 Pest Control Test of Laodelphax Striatella

A drug solution of the compound of Formula (I) at a predeterminedconcentration, which had been prepared so as to be a 50% acetone water(0.05% Tween20 available), was foliar sprayed to a rice seedling in potculture. After an air drying process, second instar larvae were releasedthereto. Thereafter, the larvae were left to stand in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C.Three days after the release, the larvae were observed for survival ordeath, and the mortality of larvae was calculated by the followingequation. Test in duplicate.Mortality (%)={number of dead larvae/(number of survived larvae+numberof dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activityhaving a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 5 Pest Control Test of Nilaparvata Lugens

A drug solution of the compound of Formula (I) at a predeterminedconcentration, which had been prepared so as to be a 50% acetone water(0.05% Tween20 available), was foliar sprayed to a rice seedling in potculture. After an air drying process, second instar larvae were releasedthereto. Thereafter, the larvae were left to stand in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C. Sixdays after the release, the larvae were observed for survival or death,and the mortality of larvae was calculated by the following equation.Test in duplicate.Mortality (%)={number of dead larvae/(number of survived larvae+numberof dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activityhaving a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 6 Pest Control Test of Sogatella Furcifera

A drug solution of the compound of Formula (I) at a predeterminedconcentration, which had been prepared so as to be a 50% acetone water(0.05% Tween20 available), was foliar sprayed to a rice seedling in potculture. After an air drying process, second instar larvae were releasedthereto. Thereafter, the larvae were left to stand in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C. Fourdays after the release, the larvae were observed for survival or death,and the mortality of larvae was calculated by the following equation.Test in duplicate.Mortality (%)={number of dead larvae/(number of survived larvae+numberof dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activityhaving a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 7 Pest Control Test of Nephotettix Cincticeps

A drug solution of the compound of Formula (I) at a predeterminedconcentration, which had been prepared so as to be a 50% acetone water(0.05% Tween20 available), was foliar sprayed to a rice seedling in potculture. After an air drying process, second instar larvae were releasedthereto. Thereafter, the larvae were left to stand in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C. Fourdays after the release, the larvae were observed for survival or death,and the mortality of larvae was calculated by the following equation.Test in duplicate.Mortality (%)={number of dead larvae/(number of survived larvae+numberof dead larvae)}×100

As a result, compound P212 exhibited insecticidal activity having amortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 8 Pest Control Test of Trialeurodes Vaporariorum

Adult greenhouse whiteflies were released to a cucumber in pot cultureand allowed to lay eggs overnight. One day after the onset of egglaying, the adults were removed and the eggs were left to stand in athermostatic chamber (16 hours of light period-8 hours of dark period)at 25° C. Three days after the completion of egg laying, a leaf diskhaving a diameter of 2.0 cm was cut out from the cucumber, it wasconfirmed that the eggs had been laid, and then a drug solution of thecompound of Formula (I) at a predetermined concentration, which had beenprepared so as to be a 50% acetone water (0.05% Tween20 available), wassprayed to the leaf disk. After the spraying, the leaf disk was left tostand in a thermostatic chamber (16 hours of light period-8 hours ofdark period) at 25° C. Fourteen days after the spraying, larvae wereobserved for survival or death, and the mortality of larvae wascalculated by the following equation. Test in duplicate.Mortality of larvae (%)={(number of eggs laid−number of survivedlarvae)/number of eggs laid)}×100

As a result, compound P212 exhibited high insecticidal activity having amortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 9 Pest Control Test of Frankliniella Occidentalis

A leaf disk having a diameter of 2.8 cm was cut out from a kidney beanin pot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed to the leaf disk.After an air drying process, first instar larvae were released to theleaf disk. Thereafter, the larvae were left to stand in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C.Three days after the release, the larvae were observed for survival ordeath, and the mortality of larvae was calculated by the followingequation. Test in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidalactivity having a mortality of 80% or higher by a foliage treatment at500 ppm.

Reference Test Example 10 Pest Control Test of TrigonotylusCaelestialium

Wheat seedling leaves and stems four days after the dissemination ofseedlings were dipped for 30 seconds in a drug solution of the compoundof Formula (I) at a predetermined concentration, which had been preparedso as to be a 50% acetone water (0.05% Tween20 available). After an airdrying process, the wheat seedling leaves and stems were placed into aglass tube, and two second instar larvae of Trigonotylus coelestialiumwere released to the same glass tube. After the larvae were released,the tube was lidded to leave the larvae to stand in a thermostaticchamber at 25° C. In order to supply water to the wheat during the test,water was given to the wheat from the bottom of the glass tube. Threedays after the treatment, the larvae were observed for survival ordeath, and the death rate of larvae was calculated by the followingequation. Test in triplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activityhaving a mortality of 80% or higher by a dipping treatment of the drugsolution at 50 ppm.

Reference Test Example 11 Pest Control Test of Plautia Crossota Stali

A drug solution of the compound of Formula (I) at a predeterminedconcentration, which had been prepared so as to be a 50% acetone water(0.05% Tween20 available), was sprayed to a young fruit of applecollected outdoors. After an air drying process, the young fruit wasplaced into a plastic cup, and two adults of Plautia crossota stali werereleased thereto. Six days after the release, the adults were observedfor survival or death, the Mortality of adults was calculated by thefollowing equation.Mortality of adults (%)={number of dead adults/(number of survivedadults+number of dead adults)}×100

As a result, compound P212 exhibited insecticidal activity having amortality of 60% or higher by a foliar treatment at 50 ppm.

Reference Test Example 12 Pest Control Test of Oulema Oryzae

1 μL (/head) of a drug solution of the compound of Formula (I) preparedat a predetermined concentration with acetone was topically applied andtreated to the back of adults collected outdoors by a micro syringe.After the drug treatment, the adults were transferred to rice seedlingsand left to stand in a thermostatic chamber at 25° C. so as to obtain 5heads per stem. Forty eight hours after the treatment, the adults wereobserved for survival or death, and the mortality of adults wascalculated by the following equation. Test in duplicate.Mortality of adults (%)={number of dead adults/(number of survivedadults+number of dead adults)}×100

As a result, compound P212 exhibited high insecticidal activity having amortality of 80% or higher in a throughput of 0.5 μg/head.

Reference Test Example 13 Pest Control Test of Musca Domestica

The backs of female adults raised indoors were treated with 1 μL (/head)of a drug solution of the compound of Formula (I) prepared at apredetermined concentration with acetone. After the drug treatment, theadults were transferred to a plastic cup and left to stand in athermostatic chamber at 25° C. so as to obtain 5 heads per cup. Twentyfour hours after the treatment, the agony situation of the adults wasobserved, and the rate of agonized adults was calculated by thefollowing equation. Test in duplicate.Mortality of adults (%)={number of dead adults/(number of survivedadults+dead adults)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidalactivity having a mortality of 80% or higher in a throughput of 2μg/head.

Soil Drench Test of Single Agent Reference Test Example 14 Pest ControlTest of Laodelphax Striatella

A rice seedling in pot culture was subjected to soil drench treatmentwith a drug solution of the compound of Formula (I) at a predeterminedconcentration, which had been prepared so as to be a 10% acetone water.Three days after the treatment, ten second instar larvae of Laodelphaxstriatella were each released thereto. Thereafter, the larvae were leftto stand in a thermostatic chamber (16 hours of light period-8 hours ofdark period) at 25° C. Three days after the release, the larvae wereobserved for survival or death, and the mortality of larvae wascalculated by the following equation. Test in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidalactivity having a mortality of 80% or higher in a throughput of 0.05mg/seedling.

Reference Test Example 15 Pest Control Test of Sogatella Furcifera

A rice seedling in pot culture was subjected to soil drench treatmentwith a drug solution of the compound of Formula (I) at a predeterminedconcentration, which had been prepared so as to be a 10% acetone water.Three days after the treatment, ten second instar larvae of Sogatellafurcifera were each released thereto. Thereafter, the larvae were leftto stand in a thermostatic chamber (16 hours of light period-8 hours ofdark period) at 25° C. Three days after the release, the larvae wereobserved for survival or death, and the mortality of larvae wascalculated by the following equation. Test in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidalactivity having a mortality of 80% or higher in a throughput of 0.05mg/seedling.

Reference Test Example 16 Pest Control Test of Nilaparvata Lugens

A rice seedling in pot culture was subjected to soil drench treatmentwith a drug solution of the compound of Formula (I), which had beenprepared so as to be a 10% acetone water. Three days after thetreatment, ten second instar larvae of Nilaparvata lugens were eachreleased thereto. Thereafter, the larvae were left to stand in athermostatic chamber (16 hours of light period-8 hours of dark period)at 25° C. Three days after the release, the larvae were observed forsurvival or death, and the mortality of larvae was calculated by thefollowing equation. Test in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidalactivity having a death rate of 80% or higher in a throughput of 0.05mg/seedling.

Reference Test Example 17 Pest Control Test of Lissorhoptrus oryzophilus

A rice seedling in pot culture was subjected to soil drench treatmentwith a drug solution of the compound of Formula (I), which had beenprepared so as to be a 10% acetone water. Two days after the treatment,five adults of Lissorhoptrus oryzophilus were each released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and themortality of larvae was calculated by the following equation. Test induplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

As a result, compound P212 exhibited high insecticidal activity having amortality of 80% or higher in a throughput of 0.1 mg/seedling.

Reference Test Example 18 Pest Control Test of Laodelphax Striatella

Wheat seedling roots forty eight hours after the dissemination of seedswere treated with a drug solution of the compound of the presentinvention at a predetermined concentration, which had been prepared soas to be a 10% acetone water. The drug was absorbed from the roots for72 hours, and then ten second instar larvae of Laodelphax striatellawere each released thereto. Thereafter, the larvae were left to stand ina thermostatic chamber (16 hours of light period-8 hours of dark period)at 25° C. Four days after the release, the larvae were observed forsurvival or death, and the mortality of larvae was calculated by thefollowing equation. The test was performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

As a result, compounds P212 and 1-204 exhibited insecticidal activityhaving a mortality of 80% or higher in a throughput of 20 μg/seedling.

The results of Reference Test Examples 1, 3 and 18 are shown in thefollowing Table.

TABLE 55 Plutella Laodelphax xylostella Aphisgossypii striatellaReference (Reference (Reference (Reference Example Test Test TestCompound Example Example Example No. Ar Y R 1) 3) 18) P-212 6-chloro- HCOCF3 100 100 100 3-pyridyl P-213 2-chloro- H COCF3 100 100 100 5-thiazolyl P-215 6-chloro- 5- COCF3 100 80 75 3-pyridyl Cl P-2166-chloro- 5-F COCF3 100 95 100 3-pyridyl P-218 2-chloro- 5- COCF3 100 605- Cl thiazolyl P-219 2-chloro- 5-F COCF3 80 85 5- thiazolyl P-2226-chloro- 4- COCF3 100 100 3-pyridyl Me P-223 6-chloro- 5- COCF3 75 753-pyridyl Me P-225 4-chloro- H COCF3 90 phenyl P-226 3-pyridyl H COCF360 100 P-227 6-chloro- H COCF3 100 100 100 5-fluoro- 3-pyridyl P-228 6-H COCF3 30 95 100 trifluoromethyl- 3- pyridyl P-229 6-fluoro- H COCF3100 100 100 3-pyridyl P-230 5,6- H COCF3 100 100 dichloro- 3-pyridylP-231 6-bromo-3- H COCF3 100 100 100 pyridyl P-232 6-chloro- 4-F COCF380 3-pyridyl P-233 6-chloro- 3-F COCF3 100 75 3-pyridyl P-234 6-chloro-H COCHCl2 100 100 100 3-pyridyl P-235 6-chloro- H COCCl3 100 95 753-pyridyl P-236 6-chloro- H COCH2Cl 100 3-pyridyl P-238 6-chloro- HCOCHF2 100 100 100 3-pyridyl P-239 6-chloro- H COCF2Cl 100 100 1003-pyridyI P-240 6-chloro- H COCHClBr 100 100 3-pyridyl P-241 6-chloro- HCOCHBr2 100 100 3-pyridyl P-242 6-chloro- H COCF2CF3 100 100 1003-pyridyl P-243 2-chloro- H COCF3 100 100 100 5- pyrimidinyl P-2446-chloro- H COCH2Br 100 100 3-pyridyl  1-20 6-chloro- H CSCF3 100 100100 3-pyridyl  1-21 6-chloro- H CSCHF2 80 100 100 3-pyridyl  1-226-chloro- H CSCF2Cl 100 100 3-pyridyl  1-23 6-chloro- H CSCF2CF3 100 1003-pyridyl  1-42 6-chloro- H C(═NOMe)CF3 100 100 100 3-pyridyl  1-1506-chloro- H C(═NCH2CH2SMe)CF3 100 100 80 3-pyridyl 3-3 6-fluoro- HCOCHF2 50 100 80 3-pyridyl 3-4 6-fluoro- H COCF2Cl 100 100 100 3-pyridyl3-5 6-fluoro- H COCF2CF3 100 55 80 3-pyridyl  3-20 6-fluoro- H CSCF3 55100 80 3-pyridyl 4-3 6-Bromo-3- H COCHF2 100 100 pyridyl 4-4 6-Bromo-3-H COCF2Cl 100 100 pyridyl 4-5 6-Bromo-3- H COCF2CF3 100 100 100 pyridyl 4-20 6-Bromo-3- H CSCF3 100 100 100 pyridyl 5-3 6Chloro- H COCHF2 100100 5fluoro- 3pyridyl 5-4 6Chloro- H COCF2Cl 100 100 5fluoro- 3pyridyl 5-20 6Chloro- H CSCF3 100 100 5fluoro- 3pyridyl 6-3 2-Cl-5- H COCHF2 80100 pyrimidinyl 6-4 2-Cl-5- H COCF3Cl 90 100 100 pyrimidiny 102-2 6-chloro- 3- COCF3 10 100 100 3-pyridyl CN

Effects Against Insecticide Resistant Pests Reference Test Example 19Pest Control Test of Nilaparvata Lugens

A rice seedling in pot culture was subjected to soil drench with asolution of the compound of Formula (I), which had been prepared so asto be a 10% acetone water. Three days after the treatment, ten secondinstar larvae of Nilaparvata lugens, which had been collected outdoorsand proliferated indoors, were each released to the rice seedling.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Six days afterthe release, the larvae were observed for survival or death, and themortality of larvae was calculated by the following equation. Test induplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

Furthermore, for comparison, the test against a species of Nilaparvatalugens which is highly susceptible to imidacloprid was performed by thesame method as described above, and the results thereof are shown inTable 45. As described in Table 45, Compound P212 and Compound 1-20exhibited high insecticidal effects against susceptible species and drugresistant species of Nilaparvata lugens, and the death rates of larvaeat 0.005 mg/seedling were (susceptible species) 100% and 100%,(resistant population I) 95% and 77% and (resistant population II) 100%and 85%, respectively. Meanwhile, the death rates of imidacloprid at0.05 mg/seedling were (susceptible species) 100%, (resistant populationI) 38% and (resistant population II) 69%, and the insecticidal effectthereof was also low even at a high dose. From the above results, itbecame obvious that Compound P212 and Compound 1-20 have highinsecticidal effects even against Nilaparvata lugens resistance againstimidacloprid.

Further, for the origin of test pests, bugs collected outdoors from theKumamoto prefecture (I) in 2007 and from the Fukuoka prefecture (II) in2005 as resistant population of Nilaparvata lugens, and bugs collectedfrom the Kagoshima prefecture and then successively reared indoors for along time as the imidacloprid susceptible population of Nilaparvatalugens were used.

TABLE 56 Insecticidal effects against Nilaparvata lugens (death rate %)Effects against Nilaparvata lugens Susceptible Resistant Resistantpopulation population I population II six days six days six daysThroughput after the after the after the (mg/seedling) treatmenttreatment treatment P212 0.05 100 100 100 0.005 100 95 100 1-20 0.01 95100 100 0.005 100 77 85 Imidacloprid 0.05 100 38 69 0.01 100 39

Mixed Agent Test Example Test Example 1 Soil Irrigation Treatment Testof Laodelphax Striatella

A rice seedling in pot culture was subjected to soil drench treatmentwith a drug solution of the compound of Formula (I) at a predeterminedconcentration, or a drug solution of a mixture of a compound of Formula(I) and an insecticide as indicated below at a predeterminedconcentration, which had been prepared so as to be a 10% acetone water.After the rice seedling was left to stand for 3 days, second instarlarvae were released thereto. Thereafter, the larvae were left to standin a thermostatic chamber (16 hours of light period-8 hours of darkperiod) at 25° C. Three days after the release, the larvae were observedfor survival or death, and the mortality of larvae was calculated by thefollowing equation. The test was performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

In addition, when there was no synergistic effect, a theoretical valuewas calculated by the Colby's equation shown as follows, and the resultsare shown in the Table.theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with CompoundP212 or Compound 1-20)

B: 100−(mortality of larvae or adults when treated only with each ofimidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin,dinotefuran, sulfoxaflor, pymetrozine, thiamethoxam, flupyradifurone andcycloxaprid))

Method for Judging Synergistic Effects

When the mortality against Laodelphax striatella in the case of amixture with another agent exceeded the theoretical value by the Colby'sequation, a synergistic effect was judged to be present.

It was demonstrated that mixed agents of the insecticides ofimidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin,dinotefuran, sulfoxaflor, pymetrozine, thiamethoxam, flupyradifurone andcycoxaprid, which were provided and tested as Compound P212, all show amortality of larvae or adults, exceed the theoretical value and havesynergistic effects.

In addition, it was demonstrated that mixed agents of the insecticidesof imidacloprid and fipronil, which were provided and tested as Compound1-20, all show a mortality of larvae or adults, exceed the theoreticalvalue and have synergistic effects.

Furthermore, it was demonstrated that mixed agents of the fungicides ofprobenazole, isotianil, tiadinil and orysastrobin, which were providedand tested as Compound P212, all exhibit insecticidal effect equal to orhigher than the insecticidal effect when treated with Compound P212alone and may be mixed and treated with a fungicide. Likewise, it wasdemonstrated that mixed agents of the fungicide of probenazole, whichwas provided and tested as Compound 1-20, exhibit insecticidal effectequal to or higher than the insecticidal effect when treated withCompound 1-20 alone and may be mixed and treated with a fungicide.

<Example of Mixed Agent with Insecticide>

TABLE 57 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 00.005 — — 0 39 Imidacloprid 0.005 0 70 Fipronil 0.005 26 65Chlorantraniliprole 0.05 9 60 Spinosad 0.5 0 62

TABLE 58 Theoretical value (%) by Colby's equation Rate Compound P212Insecticide name mg/Seedling 0 0.005 — — 0 39 Imidacloprid 0.005 0 39Fipronil 0.005 26 55 Chlorantraniliprole 0.05 9 44 Spinosad 0.5 0 39

TABLE 59 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 00.005 — — 0 18 Clothianidin 0.005 23 56 Dinotefuran 0.005 0 30Sulfoxaflor 0.005 1 63 Pymetrozine 0.05 15 89

TABLE 60 Theoretical value (%) by Colby's equation Rate Compound P212Insecticide name mg/Seedling 0 0.005 — — 0 18 Clothianidin 0.005 23 37Dinotefuran 0.005 0 18 Sulfoxaflor 0.005 1 19 Pymetrozine 0.05 15 30

TABLE 61 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 00.005 — — 0 14 Thiamethoxam 0.01 23 45

TABLE 62 Theoretical value (%) by Colby's equation Rate Compound P212Insecticide name mg/Seedling 0 0.005 — — 0 14 Thiamethoxam 0.01 23 34

TABLE 63 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 00.005 — — 0 45 Flupyradifurone 0.01 5 85

TABLE 64 Theoretical value (%) by Colby's equation Rate Compound P212Insecticide name mg/Seedling 0 0.005 — — 0 45 Flupyradifurone 0.01 5 48

TABLE 65 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound 1-20 Insecticide name mg/Seedling 00.005 — — 0 12 Imidacloprid 0.005 0 74 Fipronil 0.001 0 80

TABLE 66 Theoretical value (%) by Colby's equation Rate Compound 1-20Insecticide name mg/Seedling 0 0.005 — — 0 12 Imidacloprid 0.005 0 12Fipronil 0.001 0 12

TABLE 67 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 00.005 — — 0 0 Cycloxaprid 0.005 0 7

TABLE 68 Theoretical value (%) by Colby's equation Rate mg/ CompoundP212 Insecticide name Seedling 0 0.005 — — 0 0 Cycloxaprid 0.005 0 0

TABLE 69 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound Compound mg/ P212 1-20 Fungicidename Seedling 0 0.005 0 0.005 — — 0 39 0 8 Probenazole 0.5 9 59 9 65

TABLE 70 Theoretical value (%) by Colby's equation Rate CompoundCompound mg/ P212 1-20 Fungicide name Seedling 0 0.005 0 0.005 — — 0 390 8 Probenazole 0.5 9 44 9 16

TABLE 71 Mortality (%) of single agent and mixed agent againstLaodelphax striatella Rate Compound P212 Fungicide name mg/Seedling 00.005 — — 0 19 Isotianil 0.5 5 30 Tiadinil 0.5 8 30 Orysastrobin 0.5 470

TABLE 72 Theoretical value (%) by Colby's equation Rate Compound P212Fungicide name mg/Seedling 0 0.005 — — 0 19 Isotianil 0.5 5 23 Tiadinil0.5 8 25 Orysastrobin 0.5 4 22

Test Example 2 Foliar Treatment Test Against Laodelphax Striatella

A drug solution of the compound of Formula (I) at a predeterminedconcentration, or a drug solution of a mixture of a compound of Formula(I) and an insecticide as indicated below at a predeterminedconcentration, which had been prepared so as to be a 50% acetone water(0.05% Tween20 available), was foliar sprayed to a rice seedling in potculture. After an air drying process, second instar larvae were releasedthereto. Thereafter, the larvae were left to stand in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C.Three days after the release, the larvae were observed for survival ordeath, and the mortality of larvae was calculated by the followingequation. The test was performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

Further, when there was no synergistic effect, a theoretical value wascalculated by the Colby's equation shown as follows, and the results areshown in the Table.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with CompoundP212 or Compound 1-20)

B: 100−(mortality of larvae or adults when treated only with etofenproxor silafluofen))

Method for Judging Synergistic Effects

When the mortality against Laodelphax striatella in the case of amixture with another agent exceeded the theoretical value by the Colby'sequation, a synergistic effect was judged to be present.

It was demonstrated that mixed agents of the insecticides of etofenproxand silafluofen, which were provided and tested as Compound P212 orCompound 1-20, all show a mortality of larvae or adults approximatelyequal to the theoretical value, and may be mixed with the insecticideeven in a foliar treatment-like usage.

TABLE 73 Mortality (%) of single agent and mixed agent againstLaodelphax s striatella Compound Compound Insecticide Rate — P212 1-20name (ppm) 0 0.625 0.625 — 0 95 90 Etofenprox 10 30 90 95 Silafluofen 555 100 100

TABLE 74 Theoretical value (%) by Colby's equation Compound CompoundInsecticide Rate — P212 1-20 name (ppm) 0 0.625 0.625 — 0 95 90Etofenprox 10 30 97 93 Silafluofen 5 55 98 95

Test Example 3 Pest Control Test of Aphis Gossypii

A leaf disk having a diameter of 2.0 cm was cut out from a cucumber inpot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, or a drug solution of a mixture of acompound of Formula (I) and an insecticide as indicated below at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed thereto. After anair drying process, first instar larvae were released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and themortality of larvae was calculated by the following equation. The testwas performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

In addition, when there was no synergistic effect, a theoretical valuewas calculated by the Colby's equation shown as follows, and the resultsare shown in the Table.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with CompoundP212 or Compound 1-20)

B: 100−(mortality of larvae or adults when treated only withafidopyropen)

Method for Judging Synergistic Effects

When the mortality against Aphis gossypii in the case of a mixture withanother agent exceeded the theoretical value by the Colby's equation, asynergistic effect was judged to be present.

It was demonstrated that mixed agents of compounds of Formula (II),which were provided and tested as Compound P212 or Compound 1-20, allshow a mortality of larvae or adults, exceed the theoretical value andhave synergistic effects.

TABLE 75 Mortality (%) of single agent and mixed agent against Aphisgossypii Insecticide Rate Compound P212 Compound 1-20 name ppm 0 0.313 00.625 — — 0 45 0 19 Afidopyropen 0.002 25 70 25 40

TABLE 76 Theoretical value (%) by Colby's equation Insecticide RateCompound P212 Compound 1-20 name ppm 0 0.313 0 0.625 — — 0 45 0 19Afidopyropen 0.002 25 59 25 39

Test Example 4 Pest Control Test of Plutella Xylostella

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage inpot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, or a drug solution of a mixture of acompound of Formula (I) and an insecticide as indicated below at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed thereto. After anair drying process, second instar larvae were released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and themortality of larvae was calculated by the following equation. The testwas performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

Furthermore, when there was no synergistic effect, a theoretical valuewas calculated by the Colby's equation shown as follows, and the resultsare shown in the Table.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated with only CompoundP212)

B: 100−(mortality of larvae or adults when treated with onlyflometoquin, spinosad, fipronil, chlorantraniliprole,1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate,or afidopyropen))

Method for Judging Synergistic Effects

When the mortality against Plutella xylostella in the case of a mixturewith another agent exceeded the theoretical value by the Colby'sequation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide offlometoquin, which was provided and tested, with Compound P212, shows adeath rate of larvae or adults, exceeds the theoretical value and hassynergistic effects.

TABLE 77 Mortality (%) of single agent and mixed agent against Plutellaxylostella Rate Compound P212 Insecticide name ppm 0 1.25 — — 0 0Flometoquin 0.313 0 30

TABLE 78 Theoretical value (%) by Colby's equation Insecticide RateCompound P212 name ppm 0 1.25 — — 0 0 Flometoquin 0.313 0 0

TABLE 79 Mortality (%) of single agent and mixed agent against Plutellaxylostella Compound P212 Rate ppm Insecticide name 0 1.0 — 0 40Afidopyropen Rate 10 20 70 Spinosad ppm 0.01 11 70

TABLE 80 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 1.0 — 0 40 Afidopyropen Rate 10 20 52 Spinosadppm 0.01 11 45

TABLE 81 Mortality (%) of single agent and mixed agent against Plutellaxylostella Compound P212 Rate ppm Insecticide name 0 1.0 — 0 30Afidopyropen Rate 5 0 80 ppm

TABLE 82 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 1.0 — 0 30 Afidopyropen Rate 5 0 30 ppm

TABLE 83 Mortality (%) of single agent and mixed agent against Plutellaxylostella Compound P212 Rate ppm Insecticide name 0 2.0 — 0 60 FipronilRate 0.04 50 100 Chlorantraniliprole ppm 0.002 60 100

TABLE 84 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 2.0 — 0 60 Fipronil Rate 0.04 50 80Chlorantraniliprole ppm 0.002 60 84

TABLE 85 Mortality (%) of single agent and mixed agent against Plutellaxylostella Compound P212 Rate ppm Insecticide name 0 2.0 — 0 50 1-((6-Rate 1 30 70 chloropyridin- ppm 3-yl)methyl)-4- oxo-3-phenyl-4H-pyrido[1,2- a]pyrimidin-1- ium-2-olate Afidopyropen 5 0 100

TABLE 86 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 2.0 — 0 50 1-((6- Rate 1 30 65 chloropyridin- ppm3-yl)methyl)-4- oxo-3-phenyl- 4H-pyrido[1,2- a]pyrimidin-1- ium-2-olateAfidopyropen 5 0 50

Test Example 5 Pest Control Test of Spodoptera Litura

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage inpot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, or a drug solution of a mixture of acompound of Formula (I) and an insecticide as indicated below at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed thereto. After anair drying process, third instar larvae were released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and thelarvae mortality was calculated by the following equation. The test wasperformed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effectwas calculated using Colby's equation given below, and the results areshown in the tables.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with CompoundP212)

B: 100−(mortality of larvae or adults when treated with only theinsecticide chlorantraniliprole, emamectin benzoate, flometoquin, orafidopyropen))

Method for Judging Synergistic Effects

When the mortality against Spodoptera litura in the case of a mixturewith another agent exceeded the theoretical value given by Colby'sequation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticidechlorantraniliprole, emamectin benzoate, flometoquin, or afidopyropentested with Compound P212 shows a mortality for larvae or adults inexcess of the theoretical value and has synergistic effects.

TABLE 87 Mortality (%) of single agent and mixed agent againstSpodoptera litura (1) Compound P212 Rate ppm Insecticide name 0 20 — 040 Afidopyropen Rate 10 0 80 ppm

TABLE 88 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 20 — 0 40 Afidopyropen Rate 10 0 40 ppm

TABLE 89 Mortality (%) of single agent and mixed agent againstSpodoptera litura (2) Compound P212 Rate ppm Insecticide name 0 20 — 010 Chlorantraniliprole Rate 0.02 20 30 Emamectin benzoate ppm 0.02 0 20

TABLE 90 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 20 — 0 10 Chlorantraniliprole Rate 0.02 20 28Emamectin benzoate ppm 0.02 0 10

TABLE 91 Mortality (%) of single agent and mixed agent againstSpodoptera litura (3) Compound P212 Rate ppm Insecticide name 0 50 — 010 Flometoquin Rate 5 10 20 Afidopyropen ppm 5 0 50

TABLE 92 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 50 — 0 10 Flometoquin Rate 5 10 19 Afidopyropenppm 5 0 10

Test Example 6 Pest Control Test of Frankliniella Occidentalis

A leaf disk having a diameter of 2.8 cm was cut out from the common beanin pot culture, and a drug solution of the compound of Formula (I) at apredetermined concentration, or a drug solution of a mixture of acompound of Formula (I) and an insecticide as indicated below at apredetermined concentration, which had been prepared so as to be a 50%acetone water (0.05% Tween20 available), was sprayed thereto. After anair drying process, first instar larvae were released thereto.Thereafter, the larvae were left to stand in a thermostatic chamber (16hours of light period-8 hours of dark period) at 25° C. Three days afterthe release, the larvae were observed for survival or death, and thelarvae mortality was calculated by the following equation. The test wasperformed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effectwas calculated using Colby's equation given below, and the results areshown in the table.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with CompoundP212)

B: 100−(mortality of larvae or adults when treated with only theinsecticide imidacloprid, dinotefuran, or acetamiprid))

Method for Judging Synergistic Effects

When the mortality against Frankliniella occidentalis in the case of amixture with another agent exceeded the theoretical value given byColby's equation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide imidaclopridor dinotefuran tested with Compound P212 shows a mortality for larvae oradults in excess of the theoretical value and has synergistic effects.

TABLE 93 Mortality (%) of single agent and mixed agent againstFrankliniella occidentalis(1) Compound P212 Rate ppm Insecticide name 010 — 0 69 Imidacloprid Rate 20 69 94 ppm

TABLE 94 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 10 — 0 69 Imidacloprid Rate 20 69 90 ppm

TABLE 95 Mortality (%) of single agent and mixed agent againstFrankliniella occidentalis(2) Compound P212 Rate ppm Insecticide name 020 — 0 70 Dinotefuran Rate 5 35 85 ppm

TABLE 96 Theoretical value (%) by Colby's equation Compound P212 Rateppm Insecticide name 0 20 — 0 70 Dinotefuran Rate 5 35 81 ppm

Test Example 7 Soil Irrigation Treatment Test on Chilo Suppressalis

Rice seedlings in pot culture were submitted to a soil irrigationtreatment with a drug solution of the compound of Formula (I) at apredetermined concentration, or a drug solution of a mixture of acompound of Formula (I) and an insecticide as indicated below at apredetermined concentration, which had been prepared so as to be a 10%acetone water. After standing for 3 days, second instar larvae werereleased thereto. This was followed by standing in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C. Sixdays after the release, the larvae were observed for survival or death,and the larvae mortality was calculated by the following equation. Thetest was performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effectwas calculated using Colby's equation given below, and the results areshown in the table.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with CompoundP212)

B: 100−(mortality of larvae or adults when treated with only theinsecticide fipronil, cyantraniliprole or spinosad))

Method for Judging Synergistic Effects

When the insecticidal effect (table) against Chilo suppressalis in thecase of a mixture with another agent exceeded the theoretical valuegiven by Colby's equation, a synergistic effect was judged to bepresent.

It was demonstrated that a mixed agent of the insecticide fipronil,cyantraniliprole or spinosad tested with Compound P212 shows a mortalityfor larvae or adults in excess of the theoretical value in both casesand has synergistic effects.

TABLE 97 Mortality (%) of single agent and mixed agent against Chilosuppressalis(1) Compound P212 Rate mg/seedling Insecticide name 0 0.01 —0 33 Cyantraniliprole Rate mg/ 0.005 83 100 seedling

TABLE 98 Theoretical value (%) by Colby's equation Compound P212 Ratemg/seedling Insecticide name 0 0.01 — 0 33 Cyantraniliprole Rate mg/0.005 83 89 seedling

TABLE 99 Mortality (%) of single agent and mixed agent against Chilosuppressalis(2) Compound P212 Rate mg/seedling Insecticide name 0 0.002— 0 40 Fipronil Rate mg/ 0.0005 40 80 Chlorantraniliprole seedling0.0005 60 80 Spinosad 0.002 80 100

TABLE 100 Theoretical value (%) by Colby's equation Compound P212 Ratemg/seedling Insecticide name 0 0.002 — 0 40 Fipronil Rate mg/ 0.0005 4064 Chlorantraniliprole seedling 0.0005 60 76 Spinosad 0.002 80 88

Test Example 8 Soil Irrigation Treatment Test on Naranga Aenescens

Rice seedlings in pot culture were subjected to a soil irrigationtreatment with a drug solution of the compound of Formula (I) at apredetermined concentration, or a drug solution of a mixture of acompound of Formula (I) and an insecticide as indicated below at apredetermined concentration, which had been prepared so as to be a 10%acetone water. After standing for 3 days, first instar larvae werereleased thereto. This was followed by standing in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C. Fivedays after the release, the larvae were observed for survival or death,and the larvae mortality was calculated by the following equation. Thetest was performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effectwas calculated using Colby's equation given below, and the results areshown in the table.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with CompoundP212)

B: 100−(mortality of larvae or adults when treated with only theinsecticide spinosad or fipronil))

Method for Judging Synergistic Effects

When the mortality against Naranga aenescens in the case of a mixturewith another agent exceeded the theoretical value given by Colby'sequation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide spinosad orfipronil tested with Compound P212 shows a mortality for larvae oradults in excess of the theoretical value in all cases and hassynergistic effects.

TABLE 101 Mortality (%) of single agent and mixed agent against Narangaaenescens Compound P212 Rate mg/seedling Insecticide name 0 0.01 — 0 60Spinosad Rate mg/ 0.005 40 100 Fipronil seedling 0.01 20 80

TABLE 102 Theoretical value (%) by Colby's equation Compound P212 Ratemg/seedling Insecticide name 0 0.01 — 0 60 Spinosad Rate mg/ 0.005 40 76Fipronil seedling 0.01 20 68

Test Example 9 Test on Callosobruchus Chinensis

A compound of Formula (I) and the insecticide indicated below, preparedin predetermined concentrations using acetone, were separately topicallyapplied to the back of the same adult Callosobruchus chinensis. TheCallosobruchus chinensis was then introduced into a plastic cup and heldin a thermostatic chamber (16 hours of light period-8 hours of darkperiod) at 25° C. One day after the release, the insects were observedfor survival or death, and the insect mortality was calculated by thefollowing equation. The test was performed in duplicate.Insect mortality (%)={number of dead insects/(number of survivedinsects+number of dead insects)}×100

Furthermore, a theoretical value for the case of no synergistic effectwas calculated using Colby's equation given below, and the results areshown in the table.Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(insect mortality for treatment with only Compound P212)

B: 100−(insect mortality for treatment with only the insecticidefipronil or imidacloprid))

Method for Judging Synergistic Effects

When the mortality against Callosobruchus chinensis in the case of amixture with another agent exceeded the theoretical value given byColby's equation, a synergistic effect was judged to be present.

It was demonstrated that co-treatment with the insecticide fipronil orimidacloprid tested with Compound P212 shows an insect mortality inexcess of the theoretical value in both cases and has synergisticeffects.

TABLE 103 Mortality (%) of single agent and mixed agent againstCallosobruchus chinensis Compound P212 Rate ng/head Insecticide name 00.2 — 0 20 Fipronil Rate ng/ 0.2 0 36 Imidacloprid head 0.2 40 60

TABLE 104 Theoretical value (%) by Colby's equation Compound P212 Rateng/head Insecticide name 0 0.2 — 0 20 Fipronil Rate ng/ 0.2 0 20Imidacloprid head 0.2 40 52

Test Example 10 Pest Control Test of Rice Blast

A rice seedling in pot culture was subjected to soil irrigationtreatment with a drug solution of the compound of Formula (I) at apredetermined concentration, or a drug solution of a mixture of acompound of Formula (I) and an insecticide as indicated below at apredetermined concentration, which had been prepared with a 10% acetonewater. Three days after the treatment, a spore suspension (2×10⁵ ea/mL,0.05% Tween available) of rice blast bacteria was sprayed and inoculatedthereto, and the rice seedling was placed in a moist chamber for 24hours to promote infection. Thereafter, the larvae were left to stand ina thermostatic chamber (16 hours of light period-8 hours of dark period)at 25° C. Seven days after the inoculation, the number of lesions wasmeasured, and the preventive value was calculated by the followingequation. The test was performed in triplicate.Preventive value={(number of lesions in a zone without treatment−numberof lesions in a zone with treatment)/(number of lesions withouttreatment)}×100

As a result, it was demonstrated that in a throughput of probenazole at0.125 mg/seedling, any one mixed agent of Compound P212 and Compound1-20 exhibits insecticidal effect equal to the insecticidal effect whentreated with probenazole alone and may be mixed and treated with afungicide.

TABLE 105 Compound P212 Compound 1-20 Rate mg/seedling Insecticide name0 2.5 0 2.5 — 0 3.3 0 52.5 Probenazole Rate mg/ 0.125 96.7 93.4 96.791.8 seedling

Test Example 11 Test of Rice Blast Control (Foliar Treatment)

Rice seedlings were treated by foliar application with a drug solutionof the compound of Formula (I), or a drug solution of a mixture of acompound of Formula (I) and the fungicide indicated below, prepared in apredetermined concentration with 10% acetone water. After the treatment,a rice blast spore suspension (1.5×10⁵ ea/mL, 0.05% Tween available) wassprayed and inoculated thereto followed by holding in a thermostaticchamber (16 hours of light period-8 hours of dark period) at 25° C.Fourteen days after the inoculation, the number of lesions was measured,and the preventive value was calculated by the following equation. Thetest was performed in triplicate.Preventive value={(number of lesions in a zone without treatment−numberof lesions in a zone with treatment)/(number of lesions in a zonewithout treatment)}×100

As a result, it was demonstrated that at a treatment concentration of0.5 ppm using tiadinil, isotianil, orysastrobin, tricyclazole,diclocymet, tebufloquin, azoxystrobin or kasugamycin, the mixed agentwith Compound P212 also exhibits a fungicidal effect equal to that fortreatment with tiadinil, isotianil, orysastrobin, tricyclazole,diclocymet, tebufloquin, azoxystrobin or kasugamycin alone and a mixedtreatment with a fungicide is therefore possible.

TABLE 106 (Rice blast test 1) Compound P212 Rate ppm Fungicide name 0 50— 0 4 Tiadinil Rate 0.5 0 18 Isotianil ppm 0.5 66 72

TABLE 107 (Rice blast test 2) Compound P212 Rate ppm Fungicide name 0 50— 0 16 Orysastrobin Rate 0.5 20 91 Tricyclazole ppm 0.5 72 92 Diclocymet0.5 8 52 Tebufloquin 0.5 48 72

TABLE 108 (Rice blast test 3) Compound P212 Rate ppm Fungicide name 0 50— 0 0 Azoxystrobin Rate 0.5 37 35 Kasugamycin ppm 0.5 0 37

Test Example 12 Test of Control of Rice Sheath Blight (RhizoctoniaSolani)

Six weeks after planting, rice seedlings were subjected to foliar spraytreatment with a drug solution of the compound of Formula (I), or a drugsolution of a mixture of a compound of Formula (I) and a fungicide asindicated below, prepared in a predetermined concentration with 10%acetone water. After an air drying process, a plug of growingRhizoctonia solani (1.0 cm² agar square each) was allowed to stand atthe base of the rice. This was followed by holding in a thermostaticchamber (30° C. day-25° C. night, 16 hours of light period-8 hours ofdark period). Six days after the inoculation, the lesion height wasmeasured, and the preventive value was calculated by the followingequation. The test was performed in duplicate.Preventive value={(lesion height in a zone without treatment−lesionheight in a zone with treatment)/(lesion height in a zone withouttreatment)}×100

As a result, it was demonstrated that, at a treatment concentration of 5ppm using thifluzamide, furametpyr, pencycuron, azoxystrobin,simeconazole, validamycin, or orysastrobin, the mixed agent with ppmCompound P212 presented the same fungicidal effect as for treatment withthifluzamide, furametpyr, pencycuron, azoxystrobin, simeconazole,validamycin, or orysastrobin alone, and mixed treatment with a fungicideis therefore possible.

TABLE 109 (Sheath blight test 1) Compound P212 Rate ppm Fungicide name 050 — 0 14 Thifluzamide Rate 5 92 97 Furametpyr ppm 5 77 94 Pencycuron 569 77

TABLE 110 (Sheath blight test 2) Compound P212 Rate ppm Fungicide name 050 — 0 9 Azoxystrobin Rate 5 95 100 Simeconazole ppm 5 5 24 Validamycin5 32 74 Orysastrobin 5 72 59

Test Example 13 Test with Laodelphax Striatellus by Treatment During theVegetative Phase

Rice was planted in nursery boxes and emergence was carried out forthree days a 30° C. followed by transfer of the nursery boxes to a glassgreenhouse at 25° C. During the vegetative phase five days afterplanting, the nursery boxes were treated with a prescribed amount of amixed granule of 0.24 mg/mg probenazole (24%) and 0.02 mg/mg CompoundP212 (2%). The rice seedlings were transplanted to 1/5000a Wagner pots22 days after planting and were grown in a greenhouse at 25° C. Secondinstar larvae of Laodelphax striatellus were released at 13, 26, and 38days post-transplantation to the Wagner pots; this was followed byholding in a glass greenhouse at 25° C. Five days after the release, thelarvae were observed for survival or death, and the larvae mortality wascalculated by the following equation. The test was performed induplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

According to the results, it was shown that the mixed granule ofprobenazole and Compound P212 presented a high insecticidal effect of100% mortality and exhibited control at a practical level.

Test Example 14 Test with Laodelphax Striatellus by Soil IrrigationTreatment

Rice seedlings in pot cultivation were subjected to a soil irrigationtreatment with a drug solution of a compound of Formula (I) or a drugsolution of a mixture of a compound of Formula (I) and a paddy herbicideas indicated below, prepared in predetermined concentrations so as to bea 10% acetone water. After standing for three days, second instar larvaewere released thereto. Thereafter, the larvae were left to stand in athermostatic chamber (16 hours of light period-8 hours of dark period)at 25° C. five days after the release, the larvae were observed forsurvival or death, and the larvae mortality was calculated by thefollowing equation. The test was performed in duplicate.Mortality of larvae (%)={number of dead larvae/(number of survivedlarvae+number of dead larvae)}×100

The mixed agent of Imazosulfuron, cafenstrole, cyhalofop-butyl, daimuronand pyrazolate tested with the Compound P212 was shown in all instancesto exhibit an insecticidal effect at least equal to that for treatmentwith Compound P212 by itself, and a mixed treatment with a herbicide isthus possible.

TABLE 111 Compound P212 Rate mg/seedling Herbicide name 0 0.005 0.01 — 00 100 Imazosulfuron Rate 0.05 0 0 100 Cafenstrole mg/ 0.05 0 0 100Cyhalofop- seedling 0.05 0 0 100 butyl Daimuron 0.05 0 0 100 Pyrazolate0.05 0 0 100

Test Example 15 Test of the Control of Haemaphysalis Longicornis

A capsule with a diameter of 2 cm and a height of 2 cm was attached tothe dorsal surface of a mouse. A compound of Formula (I), ivermectin,moxidectin, permethrin, amitraz, fipronil, spinetram and the mixture ofthe compound of Formula (I) and each insecticide were dissolved inethanol at the concentrations given in Table O, and each of these wasdripped onto the surface of a mouse body within a capsule. Afterthorough drying, eight Haemaphysalis longicornis nymphs were releasedand the top of the capsule was sealed with a lid. The mouse was kept ina cage at 25° C. using a 12-hour light period and a 12-hour dark period.Five days after the release, the capsule was removed and the number ofsurviving and dead nymphs and the number of engorged individuals werecounted and the insect mortality and agonal rate was calculated by thefollowing equation.Insect mortality and agonal rate (%)={number of dead and agonalinsects/(number of survived insects+number of dead and agonalinsects)}×100

The results showed that, at a rate of 0.009 μg of ivermectin ormoxidectin, the mixed agent of either with Compound P212 also gave atick control effect that was the same as treatment with ivermectin,moxidectin, permethrin, amitraz, fipronil and spinetram alone and mixedtreatment with ivermectin, moxidectin, permethrin, amitraz, fipronil andspinetram is thus possible.

TABLE 112 Mortality (%) of single agent and mixed agent againstHaemaphysalis longicornis (1) Compound P212 Rate μg Insecticide name 01.18 — 0 53 Ivermectin Rate 0.009 3 53 Moxidectin μg 0.009 6 44

TABLE 113 Mortality (%) of single agent and mixed agent againstHaemaphysalis longicornis (2) Compound P212 Rate μg Insecticide name 01.18 — 0 60 Amitraz Rate 0.38 41 90 Permethrin μg 9.5 71 86

TABLE 114 Theoretical value (%) by Colby's equation Compound P212 Rateμg Insecticide name 0 1.18 — 0 60 Amitraz Rate 0.38 41 77 Permethrin μg9.5 71 88

TABLE 115 Mortality (%) of single agent and mixed agent againstHaemaphysalis longicornis (3) Compound P212 Rate μg Insecticide name 01.18 — 0 38 fipronil Rate 0.38 78 93 spinetoram μg 0.38 6 22

TABLE 116 Theoretical value (%) by Colby's equation Compound P212 Rateμg Insecticide name 0 1.18 — 0 38 fipronil Rate 0.38 78 86 spinetoram μg0.38 6 41

TABLE 117 Mortality (%) of single agent and mixed agent againstHaemaphysalis longicornis (4) Compound P212 Rate μg Insecticide name 01.18 — 0 18 pyriproxyfen Rate 0.0475 2 44 spinosad μg 1.9 2.5 43

TABLE 118 Theoretical value (%) by Colby's equation Compound P212 Rateμg Insecticide name 0 1.18 — 0 18 pyriproxyfen Rate 0.0475 2 20 spinosadμg 1.9 2.5 20

TABLE 119 Mortality (%) of single agent and mixed agent againstHaemaphysalis longicornis (5) Compound P212 Rate μg Insecticide name 01.18 — 0 23 imidacloprid Rate 1.9 7.7 60 dinotefuran μg 1.9 0

TABLE 120 Theoretical value (%) by Colby's equation Compound P212 Rateμg Insecticide name 0 1.18 — 0 23 imidacloprid Rate 1.9 7.7 32dinotefuran μg 1.9 0 25

What is claimed is:
 1. A pest control composition comprising: at leastone iminopyridine derivative selected from the group consisting ofN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamideand acid addition salts thereof; and at least one insecticide selectedfrom the group consisting of imidacloprid, dinotefuran, flometoquin, andagriculturally and/or zootechnically acceptable acid addition saltsthereof; wherein the at least one iminopyridine derivative: the at leastone insecticide is in a range from 0.1 to 80% by weight: 0.1 to 80% byweight.
 2. A method for protecting plants or animals from pestscomprising simultaneously or independently applying the pest controlcomposition of claim 1 to a region to be treated.
 3. A method forprotecting plants or animals from pests by treating pests, plants, seedsof plants, soil, cultivation carriers or animals as a target, with aneffective amount of the pest control composition of claim
 1. 4. A pestcontrol composition comprising: at least one iminopyridine derivativeselected from the group consisting ofN-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamideand acid addition salts thereof; and at least one other pest controlagent, wherein the other pest control agent is a control agent foranimal parasitic pests and is selected from the group consisting ofimidacloprid, dinotefuran, and agriculturally and/or zootechnicallyacceptable acid addition salts thereof; wherein the at least oneiminopyridine derivative: the control agent for animal parasitic pestsis in a range from 0.1 to 80% by weight: 0.1 to 80% by weight.
 5. Thepest control composition according to claim 1, wherein the pest is atleast one selected from the group consisting of Frankliniellaoccidentalis, Laodelphax striatella, Aphis gossypii, Plutellaxylostella; Spodoptera litura, Chilo suppressalis, Callosobruchuschinensis and Haemaphysalis longicornis.
 6. The pest control compositionaccording to claim 4, wherein the pest is at least one selected from thegroup consisting of Frankliniella occidentalis, Laodelphax striatella,Aphis gossypii, Plutella xylostella; Spodoptera litura, Chilosuppressalis, Callosobruchus chinensis and Haemaphysalis longicornis. 7.A method for protecting plants or animals from pests according to claim2, wherein the pest is at least one selected from the group consistingof Frankliniella occidentalis, Laodelphax striatella, Aphis gossypii,Plutella xylostella; Spodoptera litura, Chilo suppressalis,Callosobruchus chinensis and Haemaphysalis longicomis.
 8. A method forprotecting plants or animals from pests according to claim 3, whereinthe pest is at least one selected from the group consisting ofFrankliniella occidentalis, Laodelphax striatella, Aphis gossypii,Plutella xylostella; Spodoptera litura, Chilo suppressalis,Callosobruchus chinensis and Haemaphysalis longicomis.